# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_compound11 #TrackingRef '17034_web_deposit_cif_file_0_JohnWallis_1358639628.WALLIS_CIFFILES.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; S-3-benzyl-4-methyl-1,3-oxazolidine-2-thione, compound 11 ; _chemical_name_common ? _chemical_melting_point 350-352 _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 N O S' _chemical_formula_weight 207.28 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' S S 0.1246 0.1234 '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 P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 19.5407(9) _cell_length_b 8.0050(4) _cell_length_c 6.7851(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1061.35(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1446 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.64 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method 'Phi and Omega scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11212 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2439 _reflns_number_gt 2242 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; COLLECT (Hooft,R.W.W. 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft,R.W.W. 1998) #Although determined using DirAx, the cell is refined in the HKL #package during data reduction ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft,R.W.W. 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0261P)^2^+0.2423P] 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 0.05(7) _chemical_absolute_configuration ad # absolute configuration also known from starting material _refine_ls_number_reflns 2439 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0670 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 S1 S 0.08824(2) 0.21008(5) -0.11725(5) 0.03439(11) Uani 1 1 d . . . O1 O 0.21920(6) 0.23193(15) -0.03322(15) 0.0358(3) Uani 1 1 d . . . N1 N 0.15341(6) 0.31911(14) 0.20927(17) 0.0228(2) Uani 1 1 d . . . C1 C 0.15382(7) 0.25646(16) 0.0273(2) 0.0244(3) Uani 1 1 d . . . C2 C 0.22228(7) 0.35522(19) 0.2832(2) 0.0256(3) Uani 1 1 d . . . H2 H 0.2306 0.4784 0.2788 0.031 Uiso 1 1 calc R . . C3 C 0.26556(9) 0.2700(3) 0.1280(2) 0.0435(4) Uani 1 1 d . . . H3A H 0.3027 0.3449 0.0829 0.052 Uiso 1 1 calc R . . H3B H 0.2862 0.1664 0.1811 0.052 Uiso 1 1 calc R . . C4 C 0.23322(8) 0.2922(3) 0.4908(2) 0.0431(4) Uani 1 1 d . . . H4A H 0.2037 0.3544 0.5816 0.065 Uiso 1 1 calc R . . H4B H 0.2812 0.3082 0.5282 0.065 Uiso 1 1 calc R . . H4C H 0.2218 0.1731 0.4971 0.065 Uiso 1 1 calc R . . C5 C 0.09188(7) 0.36434(16) 0.3196(2) 0.0228(3) Uani 1 1 d . . . H5A H 0.0917 0.3040 0.4470 0.027 Uiso 1 1 calc R . . H5B H 0.0510 0.3290 0.2443 0.027 Uiso 1 1 calc R . . C6 C 0.08796(7) 0.55075(15) 0.3580(2) 0.0199(3) Uani 1 1 d . . . C7 C 0.09118(8) 0.66441(19) 0.2031(2) 0.0284(3) Uani 1 1 d . . . H7 H 0.0972 0.6253 0.0721 0.034 Uiso 1 1 calc R . . C8 C 0.08565(8) 0.83490(18) 0.2390(3) 0.0354(4) Uani 1 1 d . . . H8 H 0.0881 0.9121 0.1329 0.043 Uiso 1 1 calc R . . C9 C 0.07654(8) 0.89174(18) 0.4298(3) 0.0363(4) Uani 1 1 d . . . H9 H 0.0727 1.0082 0.4542 0.044 Uiso 1 1 calc R . . C10 C 0.07295(7) 0.78088(19) 0.5842(2) 0.0310(3) Uani 1 1 d . . . H10 H 0.0665 0.8207 0.7148 0.037 Uiso 1 1 calc R . . C11 C 0.07884(7) 0.61005(16) 0.5488(2) 0.0237(3) Uani 1 1 d . . . H11 H 0.0766 0.5336 0.6557 0.028 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 S1 0.0457(2) 0.0362(2) 0.02122(17) 0.00173(15) -0.00732(17) -0.00888(18) O1 0.0366(6) 0.0495(7) 0.0214(5) -0.0053(5) 0.0046(5) 0.0090(5) N1 0.0215(5) 0.0239(6) 0.0228(6) -0.0044(5) 0.0012(5) 0.0016(5) C1 0.0325(7) 0.0207(6) 0.0201(7) 0.0021(5) 0.0009(6) 0.0021(5) C2 0.0213(7) 0.0324(7) 0.0233(7) -0.0006(6) -0.0004(6) 0.0003(6) C3 0.0297(8) 0.0682(12) 0.0326(9) -0.0103(10) 0.0003(7) 0.0104(8) C4 0.0278(8) 0.0699(12) 0.0315(8) 0.0139(10) -0.0020(7) 0.0077(9) C5 0.0207(6) 0.0204(6) 0.0273(7) -0.0022(5) 0.0031(6) -0.0007(5) C6 0.0150(6) 0.0178(6) 0.0270(7) 0.0007(5) 0.0014(6) 0.0003(5) C7 0.0265(7) 0.0311(7) 0.0277(7) 0.0066(6) 0.0034(6) 0.0018(6) C8 0.0281(7) 0.0255(7) 0.0527(10) 0.0171(7) 0.0054(8) 0.0016(6) C9 0.0252(7) 0.0187(7) 0.0650(12) -0.0010(7) 0.0045(8) 0.0017(5) C10 0.0251(7) 0.0273(7) 0.0407(9) -0.0106(7) 0.0032(6) -0.0011(6) C11 0.0216(7) 0.0228(6) 0.0266(7) 0.0008(5) 0.0003(6) 0.0002(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 S1 C1 1.6561(15) . ? O1 C1 1.3563(18) . ? O1 C3 1.4526(19) . ? N1 C1 1.3324(18) . ? N1 C5 1.4618(17) . ? N1 C2 1.4649(18) . ? C2 C4 1.512(2) . ? C2 C3 1.513(2) . ? C5 C6 1.5168(17) . ? C6 C11 1.3904(19) . ? C6 C7 1.3917(19) . ? C7 C8 1.391(2) . ? C8 C9 1.384(3) . ? C9 C10 1.375(2) . ? C10 C11 1.3932(19) . ? 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 C1 O1 C3 109.21(11) . . ? C1 N1 C5 124.92(11) . . ? C1 N1 C2 112.69(11) . . ? C5 N1 C2 122.11(11) . . ? N1 C1 O1 109.93(12) . . ? N1 C1 S1 128.94(11) . . ? O1 C1 S1 121.13(11) . . ? N1 C2 C4 112.52(12) . . ? N1 C2 C3 100.75(11) . . ? C4 C2 C3 114.77(13) . . ? O1 C3 C2 105.66(12) . . ? N1 C5 C6 111.91(11) . . ? C11 C6 C7 119.07(12) . . ? C11 C6 C5 120.17(11) . . ? C7 C6 C5 120.73(12) . . ? C8 C7 C6 120.39(14) . . ? C9 C8 C7 119.78(14) . . ? C10 C9 C8 120.48(13) . . ? C9 C10 C11 119.87(14) . . ? C6 C11 C10 120.41(13) . . ? 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 C2 N1 C5 C6 58.97(16) . . . . ? C1 N1 C5 C6 -114.57(14) . . . . ? C4 C2 N1 C5 52.00(18) . . . . ? O1 C1 N1 C2 4.58(15) . . . . ? C1 N1 C2 C3 -11.03(15) . . . . ? N1 C2 C3 O1 12.84(16) . . . . ? C2 C3 O1 C1 -11.38(18) . . . . ? C3 O1 C1 N1 4.60(17) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.231 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 920882' ####################################################################### # # 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_compound14 #TrackingRef '17034_web_deposit_cif_file_0_JohnWallis_1358639628.WALLIS_CIFFILES.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-t-Butoxycarbonyl-4-methyl-1,3-oxazolidine-2-thione, 14 ; _chemical_name_common ? _chemical_melting_point 361-363 _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 N O3 S' _chemical_formula_weight 217.28 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.4816(2) _cell_length_b 15.2728(4) _cell_length_c 9.6621(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.115(2) _cell_angle_gamma 90.00 _cell_volume 1095.54(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2596 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker-Nonius FR591 rotating anode ; _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13919 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2506 _reflns_number_gt 2183 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0321P)^2^+0.4325P] 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 2506 _refine_ls_number_parameters 131 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.058 _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 S1 S 0.23506(4) 0.42012(2) 0.86915(4) 0.02367(10) Uani 1 1 d U . . O1 O 0.52207(11) 0.33207(5) 0.96104(9) 0.01923(19) Uani 1 1 d . . . O2 O 0.44172(11) 0.57029(6) 0.75153(10) 0.0216(2) Uani 1 1 d . . . O3 O 0.72716(11) 0.53878(5) 0.70908(9) 0.01760(19) Uani 1 1 d . . . N1 N 0.58828(12) 0.44383(6) 0.83196(10) 0.0138(2) Uani 1 1 d . . . C1 C 0.45197(15) 0.40093(8) 0.88668(12) 0.0156(2) Uani 1 1 d U . . C2 C 0.75960(14) 0.39390(8) 0.85753(12) 0.0151(2) Uani 1 1 d . . . H2 H 0.8630 0.4342 0.8858 0.018 Uiso 1 1 calc R . . C3 C 0.71855(15) 0.33869(8) 0.98055(13) 0.0193(3) Uani 1 1 d . . . H3A H 0.7749 0.2801 0.9787 0.023 Uiso 1 1 calc R . . H3B H 0.7619 0.3677 1.0701 0.023 Uiso 1 1 calc R . . C4 C 0.79410(16) 0.33968(8) 0.73177(13) 0.0204(3) Uani 1 1 d . . . H4A H 0.6953 0.2979 0.7093 0.031 Uiso 1 1 calc R . . H4B H 0.9078 0.3077 0.7530 0.031 Uiso 1 1 calc R . . H4C H 0.8015 0.3784 0.6518 0.031 Uiso 1 1 calc R . . C5 C 0.57264(15) 0.52451(7) 0.76118(12) 0.0146(2) Uani 1 1 d . . . C6 C 0.75908(16) 0.62383(8) 0.64114(12) 0.0182(3) Uani 1 1 d . . . C7 C 0.6193(2) 0.63728(10) 0.51526(14) 0.0307(3) Uani 1 1 d . . . H7A H 0.6152 0.5854 0.4552 0.046 Uiso 1 1 calc R . . H7B H 0.6514 0.6887 0.4629 0.046 Uiso 1 1 calc R . . H7C H 0.5008 0.6464 0.5463 0.046 Uiso 1 1 calc R . . C8 C 0.75992(17) 0.69616(8) 0.74850(14) 0.0219(3) Uani 1 1 d . . . H8A H 0.6400 0.7011 0.7787 0.033 Uiso 1 1 calc R . . H8B H 0.7918 0.7517 0.7072 0.033 Uiso 1 1 calc R . . H8C H 0.8484 0.6825 0.8291 0.033 Uiso 1 1 calc R . . C9 C 0.9449(2) 0.61070(9) 0.59707(17) 0.0310(3) Uani 1 1 d . . . H9A H 1.0294 0.5935 0.6782 0.047 Uiso 1 1 calc R . . H9B H 0.9856 0.6655 0.5584 0.047 Uiso 1 1 calc R . . H9C H 0.9398 0.5646 0.5261 0.047 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 S1 0.01245(15) 0.02748(19) 0.03171(19) 0.00025(13) 0.00522(12) -0.00227(11) O1 0.0184(4) 0.0175(4) 0.0226(4) 0.0046(3) 0.0059(3) -0.0012(3) O2 0.0182(4) 0.0181(4) 0.0292(5) 0.0028(4) 0.0054(4) 0.0044(3) O3 0.0181(4) 0.0132(4) 0.0231(4) 0.0032(3) 0.0090(3) 0.0002(3) N1 0.0108(4) 0.0133(5) 0.0175(5) 0.0005(4) 0.0028(4) 0.0008(4) C1 0.0164(5) 0.0152(5) 0.0156(5) -0.0024(4) 0.0037(4) -0.0024(4) C2 0.0123(5) 0.0142(5) 0.0189(6) 0.0009(4) 0.0023(4) 0.0020(4) C3 0.0177(6) 0.0201(6) 0.0201(6) 0.0032(5) 0.0026(4) 0.0025(5) C4 0.0203(6) 0.0196(6) 0.0223(6) -0.0010(5) 0.0065(5) 0.0029(5) C5 0.0159(5) 0.0138(5) 0.0143(5) -0.0016(4) 0.0026(4) -0.0010(4) C6 0.0258(6) 0.0108(5) 0.0193(6) 0.0022(5) 0.0085(5) -0.0014(5) C7 0.0468(8) 0.0265(7) 0.0178(6) 0.0041(5) 0.0002(6) -0.0053(6) C8 0.0251(6) 0.0173(6) 0.0241(6) -0.0036(5) 0.0066(5) -0.0023(5) C9 0.0357(7) 0.0189(6) 0.0438(8) 0.0011(6) 0.0260(7) -0.0017(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 S1 C1 1.6371(12) . ? O1 C1 1.3432(14) . ? O1 C3 1.4622(14) . ? O2 C5 1.1977(14) . ? O3 C5 1.3347(13) . ? O3 C6 1.4880(14) . ? N1 C1 1.3720(15) . ? N1 C5 1.4071(15) . ? N1 C2 1.4855(14) . ? C2 C4 1.5188(16) . ? C2 C3 1.5195(16) . ? C6 C8 1.5150(17) . ? C6 C7 1.5167(18) . ? C6 C9 1.5170(17) . ? 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 C1 O1 C3 109.55(9) . . ? C5 O3 C6 120.18(9) . . ? C1 N1 C5 125.76(9) . . ? C1 N1 C2 110.98(9) . . ? C5 N1 C2 123.26(9) . . ? O1 C1 N1 108.69(10) . . ? O1 C1 S1 120.79(9) . . ? N1 C1 S1 130.49(9) . . ? N1 C2 C4 112.05(9) . . ? N1 C2 C3 99.27(9) . . ? C4 C2 C3 113.21(10) . . ? O1 C3 C2 103.59(9) . . ? O2 C5 O3 127.84(11) . . ? O2 C5 N1 124.55(10) . . ? O3 C5 N1 107.61(9) . . ? O3 C6 C8 108.77(9) . . ? O3 C6 C7 109.85(10) . . ? C8 C6 C7 113.23(11) . . ? O3 C6 C9 102.19(9) . . ? C8 C6 C9 111.25(11) . . ? C7 C6 C9 110.97(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.267 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.046 _vrf_PLAT230_compound14 ; PROBLEM: Hirshfeld Test Diff for S1 -- C1 .. 7.05 su RESPONSE: A DELU instruction employed with low standard deviation did not make a great change in this value. ; _vrf_PLAT793_compound14 ; PROBLEM: The Model has Chirality at C2 (Verify) .... R RESPONSE: The material is racemic. ; _database_code_depnum_ccdc_archive 'CCDC 920883' ####################################################################### # # 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_compound17 #TrackingRef '17034_web_deposit_cif_file_0_JohnWallis_1358639628.WALLIS_CIFFILES.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-t-Butoxycarbonyl-4-methyl-1,3-oxazolidine-2-one, 17 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 N O4' _chemical_formula_weight 201.22 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 Pbca 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' '-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 9.1981(4) _cell_length_b 9.2778(3) _cell_length_c 23.4543(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2001.55(14) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3213 _cell_measurement_theta_min 3.1123 _cell_measurement_theta_max 29.2751 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3427 _exptl_crystal_size_mid 0.2741 _exptl_crystal_size_min 0.0660 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 15.9832 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6386 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 29.34 _reflns_number_total 2376 _reflns_number_gt 1819 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0354P)^2^+1.1231P] 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 2376 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.10835(12) 0.32534(13) 0.51204(5) 0.0227(3) Uani 1 1 d . . . O2 O -0.10666(13) 0.42992(13) 0.34704(5) 0.0264(3) Uani 1 1 d . . . O3 O 0.08560(11) 0.57250(12) 0.36955(5) 0.0171(3) Uani 1 1 d . . . O4 O 0.22889(12) 0.49854(13) 0.46627(5) 0.0231(3) Uani 1 1 d . . . N1 N 0.02890(14) 0.38191(14) 0.42528(6) 0.0161(3) Uani 1 1 d . . . C1 C 0.13191(17) 0.41217(17) 0.46688(7) 0.0167(3) Uani 1 1 d . . . C3 C -0.01704(19) 0.23386(18) 0.50297(7) 0.0214(4) Uani 1 1 d . . . H3A H -0.0955 0.2587 0.5301 0.026 Uiso 1 1 calc R . . H3B H 0.0093 0.1313 0.5084 0.026 Uiso 1 1 calc R . . C2 C -0.06661(17) 0.26078(17) 0.44153(7) 0.0167(3) Uani 1 1 d . . . H2 H -0.1704 0.2927 0.4412 0.020 Uiso 1 1 calc R . . C4 C -0.0480(2) 0.12964(18) 0.40380(7) 0.0230(4) Uani 1 1 d . . . H4A H -0.0714 0.1552 0.3643 0.034 Uiso 1 1 calc R . . H4B H -0.1134 0.0529 0.4167 0.034 Uiso 1 1 calc R . . H4C H 0.0528 0.0960 0.4059 0.034 Uiso 1 1 calc R . . C5 C -0.00497(17) 0.46300(17) 0.37672(7) 0.0168(3) Uani 1 1 d . . . C6 C 0.05719(17) 0.67953(17) 0.32339(7) 0.0167(3) Uani 1 1 d . . . C7 C -0.08812(18) 0.75172(19) 0.33365(8) 0.0232(4) Uani 1 1 d . . . H7A H -0.1664 0.6816 0.3280 0.035 Uiso 1 1 calc R . . H7B H -0.1002 0.8318 0.3068 0.035 Uiso 1 1 calc R . . H7C H -0.0918 0.7885 0.3728 0.035 Uiso 1 1 calc R . . C8 C 0.0662(2) 0.6080(2) 0.26524(7) 0.0260(4) Uani 1 1 d . . . H8A H 0.1589 0.5566 0.2618 0.039 Uiso 1 1 calc R . . H8B H 0.0597 0.6816 0.2354 0.039 Uiso 1 1 calc R . . H8C H -0.0142 0.5395 0.2610 0.039 Uiso 1 1 calc R . . C9 C 0.18147(19) 0.78523(19) 0.33121(8) 0.0258(4) Uani 1 1 d . . . H9A H 0.1752 0.8291 0.3691 0.039 Uiso 1 1 calc R . . H9B H 0.1752 0.8607 0.3021 0.039 Uiso 1 1 calc R . . H9C H 0.2743 0.7342 0.3275 0.039 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 0.0233(6) 0.0249(6) 0.0199(6) 0.0053(5) -0.0025(5) -0.0027(5) O2 0.0266(7) 0.0220(6) 0.0306(7) 0.0080(6) -0.0122(5) -0.0086(6) O3 0.0179(6) 0.0141(5) 0.0195(6) 0.0050(5) -0.0027(5) -0.0026(5) O4 0.0179(6) 0.0260(6) 0.0253(7) 0.0029(6) -0.0035(5) -0.0043(5) N1 0.0162(6) 0.0130(7) 0.0190(7) 0.0028(6) -0.0010(5) -0.0016(5) C1 0.0164(8) 0.0156(8) 0.0179(8) 0.0000(7) 0.0008(6) 0.0055(7) C3 0.0289(9) 0.0144(8) 0.0209(9) 0.0024(7) 0.0003(7) -0.0033(7) C2 0.0144(7) 0.0134(7) 0.0223(8) 0.0039(7) 0.0018(6) -0.0008(6) C4 0.0306(9) 0.0144(8) 0.0238(9) 0.0002(7) -0.0019(7) -0.0027(7) C5 0.0168(8) 0.0123(8) 0.0213(8) 0.0006(7) -0.0003(7) 0.0004(6) C6 0.0195(8) 0.0136(7) 0.0170(8) 0.0044(6) -0.0016(6) -0.0014(7) C7 0.0227(9) 0.0194(8) 0.0275(9) 0.0049(7) 0.0000(7) 0.0017(7) C8 0.0334(10) 0.0242(9) 0.0202(9) 0.0019(7) 0.0009(8) 0.0014(8) C9 0.0253(9) 0.0227(9) 0.0294(10) 0.0088(8) -0.0047(7) -0.0063(8) _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 C1 1.3483(19) . ? O1 C3 1.448(2) . ? O2 C5 1.2056(19) . ? O3 C5 1.3245(19) . ? O3 C6 1.4922(19) . ? O4 C1 1.1992(19) . ? N1 C1 1.389(2) . ? N1 C5 1.400(2) . ? N1 C2 1.477(2) . ? C2 C3 1.532(2) . ? C2 C4 1.514(2) . ? C6 C7 1.514(2) . ? C6 C9 1.517(2) . ? C6 C8 1.519(2) . ? 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 C1 O1 C3 111.28(12) . . ? C5 O3 C6 119.49(12) . . ? C1 N1 C5 127.94(13) . . ? C1 N1 C2 112.24(13) . . ? C5 N1 C2 119.11(13) . . ? O4 C1 O1 121.88(15) . . ? O4 C1 N1 129.36(15) . . ? O1 C1 N1 108.75(13) . . ? N1 C2 C4 113.18(13) . . ? N1 C2 C3 100.94(12) . . ? C4 C2 C3 112.65(13) . . ? O1 C3 C2 106.25(12) . . ? O2 C5 O3 127.59(15) . . ? O2 C5 N1 120.37(14) . . ? O3 C5 N1 112.04(13) . . ? O3 C6 C7 109.49(13) . . ? O3 C6 C9 102.15(12) . . ? C7 C6 C9 111.10(14) . . ? O3 C6 C8 110.56(13) . . ? C7 C6 C8 112.58(14) . . ? C9 C6 C8 110.48(14) . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.242 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 920884' ####################################################################### # # 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_compound31 #TrackingRef '17034_web_deposit_cif_file_0_JohnWallis_1358639628.WALLIS_CIFFILES.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Butoxycarbonyl-4-methylthiazolidin-2-one, compound 31 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 N O3 S' _chemical_formula_weight 217.28 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.6972(6) _cell_length_b 6.7661(3) _cell_length_c 17.4884(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.177(5) _cell_angle_gamma 90.00 _cell_volume 1129.40(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2312 _cell_measurement_theta_min 3.0046 _cell_measurement_theta_max 27.2793 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3627 _exptl_crystal_size_mid 0.2459 _exptl_crystal_size_min 0.1817 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 15.9832 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4666 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.34 _reflns_number_total 2390 _reflns_number_gt 1996 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0506P)^2^+1.1988P] 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 2390 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 S1 S 0.88971(7) 0.87212(9) 0.07789(3) 0.03011(19) Uani 1 1 d . . . O1 O 0.7157(2) 1.3319(2) -0.10148(10) 0.0363(4) Uani 1 1 d . . . O2 O 0.82636(18) 1.2471(2) 0.05216(9) 0.0292(4) Uani 1 1 d . . . O3 O 0.59350(17) 1.0683(3) -0.15717(9) 0.0304(4) Uani 1 1 d . . . N4 N 0.73760(18) 1.0233(2) -0.04533(10) 0.0184(4) Uani 1 1 d . . . C5 C 0.6830(2) 1.1614(3) -0.10259(12) 0.0199(4) Uani 1 1 d . . . C6 C 0.7110(2) 0.8071(3) -0.05335(12) 0.0203(4) Uani 1 1 d . . . H6 H 0.7063 0.7688 -0.1090 0.024 Uiso 1 1 calc R . . C7 C 0.8135(2) 1.0815(3) 0.02615(12) 0.0220(5) Uani 1 1 d . . . C8 C 0.5737(3) 0.7507(3) -0.02834(14) 0.0287(5) Uani 1 1 d . . . H8A H 0.5785 0.7837 0.0266 0.043 Uiso 1 1 calc R . . H8B H 0.5577 0.6085 -0.0358 0.043 Uiso 1 1 calc R . . H8C H 0.4965 0.8238 -0.0597 0.043 Uiso 1 1 calc R . . C9 C 0.8386(3) 0.7101(3) -0.00477(14) 0.0276(5) Uani 1 1 d . . . H9A H 0.9153 0.6975 -0.0350 0.033 Uiso 1 1 calc R . . H9B H 0.8148 0.5769 0.0125 0.033 Uiso 1 1 calc R . . C10 C 0.5223(3) 1.1740(4) -0.22803(13) 0.0345(6) Uani 1 1 d . . . C11 C 0.6274(3) 1.2471(4) -0.27417(15) 0.0373(6) Uani 1 1 d . . . H11A H 0.6856 1.3492 -0.2446 0.056 Uiso 1 1 calc R . . H11B H 0.5787 1.3030 -0.3233 0.056 Uiso 1 1 calc R . . H11C H 0.6868 1.1371 -0.2849 0.056 Uiso 1 1 calc R . . C12 C 0.4381(6) 1.0092(7) -0.2715(2) 0.122(2) Uani 1 1 d . . . H12A H 0.3899 1.0583 -0.3219 0.183 Uiso 1 1 calc R . . H12B H 0.3689 0.9616 -0.2412 0.183 Uiso 1 1 calc R . . H12C H 0.5008 0.9006 -0.2796 0.183 Uiso 1 1 calc R . . C13 C 0.4335(4) 1.3371(9) -0.20585(19) 0.107(2) Uani 1 1 d . . . H13A H 0.4935 1.4376 -0.1764 0.160 Uiso 1 1 calc R . . H13B H 0.3690 1.2839 -0.1738 0.160 Uiso 1 1 calc R . . H13C H 0.3798 1.3970 -0.2529 0.160 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 S1 0.0412(4) 0.0214(3) 0.0240(3) 0.0044(2) -0.0047(2) 0.0008(2) O1 0.0602(12) 0.0167(8) 0.0262(9) 0.0019(7) -0.0083(8) 0.0000(8) O2 0.0419(10) 0.0184(8) 0.0236(8) -0.0034(6) -0.0040(7) -0.0035(7) O3 0.0323(9) 0.0377(10) 0.0176(8) 0.0076(7) -0.0056(6) -0.0155(7) N4 0.0230(9) 0.0145(9) 0.0169(8) -0.0004(7) 0.0011(7) -0.0026(7) C5 0.0211(10) 0.0212(11) 0.0173(10) -0.0009(8) 0.0031(8) 0.0020(8) C6 0.0281(11) 0.0149(10) 0.0191(10) -0.0025(8) 0.0072(8) -0.0057(8) C7 0.0265(11) 0.0195(11) 0.0191(10) 0.0018(8) 0.0017(9) -0.0038(8) C8 0.0349(13) 0.0252(12) 0.0293(12) -0.0043(10) 0.0143(10) -0.0095(10) C9 0.0369(13) 0.0156(11) 0.0299(12) -0.0016(9) 0.0049(10) -0.0009(9) C10 0.0284(12) 0.0545(16) 0.0175(11) 0.0141(11) -0.0042(9) -0.0078(11) C11 0.0391(14) 0.0462(16) 0.0279(13) 0.0143(11) 0.0095(11) 0.0059(12) C12 0.151(4) 0.125(4) 0.057(2) 0.055(3) -0.073(3) -0.106(4) C13 0.079(3) 0.211(6) 0.0343(17) 0.039(3) 0.0206(17) 0.105(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 S1 C7 1.771(2) . ? S1 C9 1.812(2) . ? O1 C5 1.196(3) . ? O2 C7 1.207(3) . ? O3 C5 1.330(3) . ? O3 C10 1.490(3) . ? N4 C7 1.391(3) . ? N4 C5 1.403(3) . ? N4 C6 1.488(3) . ? C6 C9 1.521(3) . ? C6 C8 1.521(3) . ? C10 C11 1.491(3) . ? C10 C13 1.493(5) . ? C10 C12 1.505(4) . ? 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 C7 S1 C9 92.63(10) . . ? C5 O3 C10 121.18(18) . . ? C7 N4 C5 121.72(17) . . ? C7 N4 C6 114.75(17) . . ? C5 N4 C6 123.38(17) . . ? O1 C5 O3 127.3(2) . . ? O1 C5 N4 124.44(19) . . ? O3 C5 N4 108.25(17) . . ? N4 C6 C9 105.14(16) . . ? N4 C6 C8 111.43(18) . . ? C9 C6 C8 113.46(19) . . ? O2 C7 N4 127.2(2) . . ? O2 C7 S1 122.97(17) . . ? N4 C7 S1 109.84(15) . . ? C6 C9 S1 105.39(15) . . ? O3 C10 C11 110.42(19) . . ? O3 C10 C13 110.0(2) . . ? C11 C10 C13 112.1(3) . . ? O3 C10 C12 101.2(2) . . ? C11 C10 C12 109.5(3) . . ? C13 C10 C12 113.1(4) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 26.75 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.525 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.074 _vrf_PLAT213_compound31 ; PROBLEM: Atom C12 has ADP max/min Ratio ..... 4.6 prola RESPONSE: The t-butyl group has two carbon atoms with long ADPs, C12 and C13,but one near spherical. There is a intermolecular contact (C--C, 3.74 Ang) between two of the former, so there may be mutual distortions to minimise this interaction. ; _database_code_depnum_ccdc_archive 'CCDC 920885' ####################################################################### # # 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_compound35 #TrackingRef '17034_web_deposit_cif_file_0_JohnWallis_1358639628.WALLIS_CIFFILES.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (+/-)N-(t-Butoxycarbonyl)-O-(2',2'-dimethylpropanethiocarbonyl)-alaninol compound 35 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H25 N O3 S' _chemical_formula_weight 275.40 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4804(3) _cell_length_b 9.9540(3) _cell_length_c 28.7919(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3290.22(16) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9968 _cell_measurement_theta_min 2.9424 _cell_measurement_theta_max 29.1531 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.112 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 15.9832 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 23932 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0713 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.9424 _diffrn_reflns_theta_max 29.1531 _reflns_number_total 7791 _reflns_number_gt 5508 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The structure was refined as a twin with the twin law TWIN 1 0 0 0 -1 0 0 0 -1 and BASF 0.40879 ; _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^)+(0.0953P)^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 7791 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1595 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 S1A S 0.82391(9) 0.91557(14) 0.18415(3) 0.0723(4) Uani 1 1 d . . . O1A O 0.63879(17) 0.9630(2) 0.13529(6) 0.0300(5) Uani 1 1 d . . . O2A O 0.74332(18) 0.83199(17) -0.00014(7) 0.0319(5) Uani 1 1 d . . . O3A O 0.81317(19) 1.00227(16) -0.04486(6) 0.0294(5) Uani 1 1 d . . . N1A N 0.7024(2) 1.0497(2) 0.01495(7) 0.0237(5) Uani 1 1 d . . . H1A H 0.7121 1.1333 0.0058 0.028 Uiso 1 1 calc R . . C1A C 0.4902(4) 0.9933(5) 0.20645(16) 0.0736(14) Uani 1 1 d . . . H1A1 H 0.4309 0.9724 0.2299 0.110 Uiso 1 1 calc R . . H1A2 H 0.4559 0.9861 0.1754 0.110 Uiso 1 1 calc R . . H1A3 H 0.5189 1.0850 0.2113 0.110 Uiso 1 1 calc R . . C2A C 0.6394(4) 0.8935(6) 0.25946(12) 0.0900(18) Uani 1 1 d . . . H2A1 H 0.6931 0.8179 0.2634 0.135 Uiso 1 1 calc R . . H2A2 H 0.5749 0.8848 0.2816 0.135 Uiso 1 1 calc R . . H2A3 H 0.6809 0.9779 0.2652 0.135 Uiso 1 1 calc R . . C3A C 0.5438(4) 0.7565(4) 0.19812(14) 0.0702(13) Uani 1 1 d . . . H3A1 H 0.6063 0.6896 0.1993 0.105 Uiso 1 1 calc R . . H3A2 H 0.5113 0.7597 0.1667 0.105 Uiso 1 1 calc R . . H3A3 H 0.4824 0.7317 0.2202 0.105 Uiso 1 1 calc R . . C4A C 0.5922(3) 0.8934(3) 0.21088(10) 0.0337(7) Uani 1 1 d . . . C5A C 0.6864(3) 0.9271(3) 0.17541(9) 0.0321(6) Uani 1 1 d . . . C6A C 0.7122(2) 1.0007(3) 0.09685(9) 0.0296(6) Uani 1 1 d . . . H6A1 H 0.7689 0.9285 0.0900 0.035 Uiso 1 1 calc R . . H6A2 H 0.7556 1.0840 0.1041 0.035 Uiso 1 1 calc R . . C7A C 0.6316(2) 1.0228(3) 0.05569(9) 0.0235(6) Uani 1 1 d . . . H7A H 0.5867 0.9382 0.0502 0.028 Uiso 1 1 calc R . . C8A C 0.5458(3) 1.1363(3) 0.06328(11) 0.0347(7) Uani 1 1 d . . . H8A1 H 0.5883 1.2210 0.0671 0.052 Uiso 1 1 calc R . . H8A2 H 0.4997 1.1184 0.0913 0.052 Uiso 1 1 calc R . . H8A3 H 0.4937 1.1430 0.0364 0.052 Uiso 1 1 calc R . . C9A C 0.7534(2) 0.9503(3) -0.00909(9) 0.0210(6) Uani 1 1 d . . . C10A C 0.8719(3) 0.9141(3) -0.07886(10) 0.0293(7) Uani 1 1 d . . . C11A C 0.9229(4) 1.0145(3) -0.11217(14) 0.0580(11) Uani 1 1 d . . . H11A H 0.8600 1.0665 -0.1265 0.087 Uiso 1 1 calc R . . H11B H 0.9667 0.9671 -0.1364 0.087 Uiso 1 1 calc R . . H11C H 0.9752 1.0753 -0.0954 0.087 Uiso 1 1 calc R . . C12A C 0.7851(3) 0.8236(4) -0.10244(12) 0.0516(10) Uani 1 1 d . . . H12A H 0.7550 0.7583 -0.0800 0.077 Uiso 1 1 calc R . . H12B H 0.8232 0.7760 -0.1281 0.077 Uiso 1 1 calc R . . H12C H 0.7206 0.8776 -0.1146 0.077 Uiso 1 1 calc R . . C13A C 0.9678(3) 0.8367(4) -0.05541(14) 0.0553(10) Uani 1 1 d . . . H13A H 1.0136 0.8976 -0.0359 0.083 Uiso 1 1 calc R . . H13B H 1.0183 0.7962 -0.0790 0.083 Uiso 1 1 calc R . . H13C H 0.9338 0.7658 -0.0361 0.083 Uiso 1 1 calc R . . S1B S 0.66801(8) 0.33591(10) 0.17683(4) 0.0566(3) Uani 1 1 d . . . O1B O 0.8460(2) 0.4601(3) 0.14098(8) 0.0526(7) Uani 1 1 d . . . O2B O 0.76133(19) 0.33238(16) 0.00174(7) 0.0337(5) Uani 1 1 d . . . O3B O 0.69237(19) 0.50332(16) -0.04334(6) 0.0301(5) Uani 1 1 d . . . N1B N 0.7910(2) 0.5508(2) 0.02012(8) 0.0285(6) Uani 1 1 d . . . H1B H 0.7783 0.6348 0.0120 0.034 Uiso 1 1 calc R . . C1B C 0.8992(4) 0.5296(4) 0.23676(15) 0.0715(14) Uani 1 1 d . . . H1B1 H 0.9198 0.5926 0.2119 0.107 Uiso 1 1 calc R . . H1B2 H 0.9609 0.5292 0.2603 0.107 Uiso 1 1 calc R . . H1B3 H 0.8256 0.5575 0.2511 0.107 Uiso 1 1 calc R . . C2B C 0.8443(3) 0.2950(4) 0.25489(11) 0.0510(9) Uani 1 1 d . . . H2B1 H 0.7721 0.3302 0.2684 0.077 Uiso 1 1 calc R . . H2B2 H 0.9041 0.2889 0.2791 0.077 Uiso 1 1 calc R . . H2B3 H 0.8299 0.2055 0.2419 0.077 Uiso 1 1 calc R . . C3B C 1.0014(3) 0.3357(4) 0.19745(12) 0.0559(10) Uani 1 1 d . . . H3B1 H 0.9903 0.2445 0.1854 0.084 Uiso 1 1 calc R . . H3B2 H 1.0596 0.3343 0.2224 0.084 Uiso 1 1 calc R . . H3B3 H 1.0284 0.3945 0.1723 0.084 Uiso 1 1 calc R . . C4B C 0.8858(3) 0.3887(3) 0.21654(11) 0.0344(7) Uani 1 1 d . . . C5B C 0.7989(3) 0.3992(3) 0.17688(10) 0.0329(7) Uani 1 1 d . . . C6B C 0.7768(3) 0.4917(4) 0.10025(11) 0.0523(10) Uani 1 1 d . . . H6B1 H 0.7256 0.5695 0.1066 0.063 Uiso 1 1 calc R . . H6B2 H 0.7274 0.4140 0.0917 0.063 Uiso 1 1 calc R . . C7B C 0.8579(3) 0.5233(3) 0.06242(10) 0.0299(7) Uani 1 1 d . . . H7B H 0.9071 0.4421 0.0566 0.036 Uiso 1 1 calc R . . C8B C 0.9383(3) 0.6402(4) 0.07264(13) 0.0521(10) Uani 1 1 d . . . H8B1 H 0.9942 0.6504 0.0472 0.078 Uiso 1 1 calc R . . H8B2 H 0.9804 0.6232 0.1017 0.078 Uiso 1 1 calc R . . H8B3 H 0.8924 0.7227 0.0757 0.078 Uiso 1 1 calc R . . C9B C 0.7486(2) 0.4514(3) -0.00656(10) 0.0236(6) Uani 1 1 d . . . C10B C 0.6347(2) 0.4184(3) -0.07817(10) 0.0260(6) Uani 1 1 d . . . C11B C 0.5853(3) 0.5196(3) -0.11177(12) 0.0460(9) Uani 1 1 d . . . H11D H 0.5308 0.5788 -0.0954 0.069 Uiso 1 1 calc R . . H11E H 0.5443 0.4726 -0.1368 0.069 Uiso 1 1 calc R . . H11F H 0.6488 0.5733 -0.1250 0.069 Uiso 1 1 calc R . . C12B C 0.7253(3) 0.3303(4) -0.10219(13) 0.0520(10) Uani 1 1 d . . . H12D H 0.7867 0.3872 -0.1153 0.078 Uiso 1 1 calc R . . H12E H 0.6880 0.2789 -0.1271 0.078 Uiso 1 1 calc R . . H12F H 0.7595 0.2683 -0.0795 0.078 Uiso 1 1 calc R . . C13B C 0.5394(3) 0.3381(4) -0.05637(12) 0.0473(9) Uani 1 1 d . . . H13D H 0.5731 0.2725 -0.0348 0.071 Uiso 1 1 calc R . . H13E H 0.4956 0.2908 -0.0806 0.071 Uiso 1 1 calc R . . H13F H 0.4869 0.3982 -0.0394 0.071 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 S1A 0.0317(4) 0.1454(11) 0.0399(5) 0.0257(6) -0.0031(4) -0.0026(6) O1A 0.0261(11) 0.0425(11) 0.0215(10) 0.0023(9) 0.0042(8) -0.0004(8) O2A 0.0419(12) 0.0174(11) 0.0364(11) 0.0034(8) 0.0102(10) 0.0033(9) O3A 0.0399(12) 0.0149(9) 0.0334(11) -0.0010(8) 0.0187(10) 0.0009(8) N1A 0.0328(13) 0.0147(11) 0.0237(11) 0.0031(9) 0.0077(10) -0.0013(9) C1A 0.066(3) 0.078(3) 0.076(3) 0.012(2) 0.051(2) 0.016(2) C2A 0.067(3) 0.181(5) 0.0224(18) -0.006(2) 0.0056(18) -0.039(3) C3A 0.099(3) 0.054(2) 0.058(3) -0.0032(19) 0.019(2) -0.034(2) C4A 0.0416(18) 0.0405(17) 0.0189(14) -0.0003(12) 0.0075(12) -0.0102(14) C5A 0.0357(16) 0.0399(16) 0.0207(14) -0.0064(13) 0.0009(13) -0.0013(13) C6A 0.0269(14) 0.0388(15) 0.0230(14) 0.0028(12) 0.0063(11) 0.0003(12) C7A 0.0242(13) 0.0239(14) 0.0223(14) -0.0021(11) 0.0042(11) -0.0016(11) C8A 0.0271(16) 0.0459(18) 0.0312(16) 0.0045(13) 0.0069(12) 0.0116(13) C9A 0.0236(14) 0.0147(14) 0.0247(14) 0.0021(11) 0.0023(11) 0.0010(11) C10A 0.0310(15) 0.0257(15) 0.0314(16) -0.0084(12) 0.0149(13) 0.0020(12) C11A 0.080(3) 0.0362(19) 0.058(2) -0.0013(17) 0.046(2) -0.0048(19) C12A 0.048(2) 0.062(2) 0.044(2) -0.0248(18) 0.0174(17) -0.0187(17) C13A 0.0332(19) 0.069(3) 0.064(2) -0.002(2) 0.0071(18) 0.0161(18) S1B 0.0373(5) 0.0819(7) 0.0504(5) 0.0093(5) -0.0083(4) -0.0076(5) O1B 0.0367(14) 0.0828(18) 0.0382(13) 0.0221(12) -0.0213(11) -0.0198(12) O2B 0.0473(13) 0.0125(10) 0.0412(12) 0.0022(8) -0.0190(10) 0.0008(9) O3B 0.0446(13) 0.0142(9) 0.0316(11) 0.0013(8) -0.0185(10) -0.0004(8) N1B 0.0422(14) 0.0130(11) 0.0302(13) 0.0009(9) -0.0185(11) 0.0000(10) C1B 0.104(4) 0.044(2) 0.066(3) -0.0087(19) -0.052(3) 0.000(2) C2B 0.056(2) 0.062(2) 0.0358(18) 0.0102(16) -0.0039(16) 0.0051(18) C3B 0.041(2) 0.088(3) 0.0389(19) 0.0084(19) -0.0084(16) 0.0130(19) C4B 0.0374(17) 0.0377(17) 0.0280(16) -0.0069(13) -0.0114(13) 0.0002(14) C5B 0.0331(16) 0.0401(16) 0.0257(15) -0.0015(13) -0.0046(12) 0.0046(12) C6B 0.0349(19) 0.085(3) 0.0367(19) 0.0153(18) -0.0211(15) -0.0087(17) C7B 0.0365(17) 0.0206(14) 0.0324(16) -0.0008(12) -0.0170(13) 0.0051(11) C8B 0.052(2) 0.060(2) 0.044(2) 0.0107(17) -0.0218(17) -0.0205(18) C9B 0.0243(14) 0.0179(14) 0.0286(15) -0.0011(12) -0.0084(11) 0.0004(11) C10B 0.0320(15) 0.0162(14) 0.0300(15) -0.0009(11) -0.0147(12) -0.0010(11) C11B 0.066(2) 0.0291(16) 0.043(2) 0.0024(15) -0.0295(18) -0.0033(16) C12B 0.044(2) 0.068(3) 0.044(2) -0.0224(18) -0.0132(17) 0.0124(17) C13B 0.046(2) 0.058(2) 0.0380(18) 0.0140(17) -0.0158(16) -0.0177(17) _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 S1A C5A 1.602(3) . ? O1A C5A 1.327(3) . ? O1A C6A 1.441(3) . ? O2A C9A 1.211(3) . ? O3A C9A 1.342(3) . ? O3A C10A 1.477(3) . ? N1A C9A 1.342(3) . ? N1A C7A 1.452(3) . ? N1A H1A 0.8800 . ? C1A C4A 1.542(5) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2A C4A 1.500(5) . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? C3A C4A 1.518(5) . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? C4A C5A 1.525(4) . ? C6A C7A 1.520(4) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A C8A 1.515(4) . ? C7A H7A 1.0000 . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C10A C11A 1.503(4) . ? C10A C13A 1.503(5) . ? C10A C12A 1.505(4) . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? S1B C5B 1.629(3) . ? O1B C5B 1.315(4) . ? O1B C6B 1.451(3) . ? O2B C9B 1.218(3) . ? O3B C9B 1.343(3) . ? O3B C10B 1.469(3) . ? N1B C9B 1.344(3) . ? N1B C7B 1.466(3) . ? N1B H1B 0.8800 . ? C1B C4B 1.526(5) . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? C2B C4B 1.522(5) . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? C3B C4B 1.530(5) . ? C3B H3B1 0.9800 . ? C3B H3B2 0.9800 . ? C3B H3B3 0.9800 . ? C4B C5B 1.520(4) . ? C6B C7B 1.467(5) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B C8B 1.515(4) . ? C7B H7B 1.0000 . ? C8B H8B1 0.9800 . ? C8B H8B2 0.9800 . ? C8B H8B3 0.9800 . ? C10B C13B 1.494(4) . ? C10B C11B 1.507(4) . ? C10B C12B 1.526(4) . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 0.9800 . ? 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 C5A O1A C6A 119.8(2) . . ? C9A O3A C10A 120.87(19) . . ? C9A N1A C7A 121.7(2) . . ? C9A N1A H1A 119.2 . . ? C7A N1A H1A 119.2 . . ? C4A C1A H1A1 109.5 . . ? C4A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C4A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C4A C2A H2A1 109.5 . . ? C4A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C4A C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C4A C3A H3A1 109.5 . . ? C4A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C4A C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? C2A C4A C3A 111.0(3) . . ? C2A C4A C5A 111.6(3) . . ? C3A C4A C5A 107.2(3) . . ? C2A C4A C1A 110.5(4) . . ? C3A C4A C1A 106.3(3) . . ? C5A C4A C1A 110.0(3) . . ? O1A C5A C4A 110.5(2) . . ? O1A C5A S1A 124.2(2) . . ? C4A C5A S1A 125.3(2) . . ? O1A C6A C7A 106.3(2) . . ? O1A C6A H6A1 110.5 . . ? C7A C6A H6A1 110.5 . . ? O1A C6A H6A2 110.5 . . ? C7A C6A H6A2 110.5 . . ? H6A1 C6A H6A2 108.7 . . ? N1A C7A C8A 110.1(2) . . ? N1A C7A C6A 108.4(2) . . ? C8A C7A C6A 113.1(2) . . ? N1A C7A H7A 108.4 . . ? C8A C7A H7A 108.4 . . ? C6A C7A H7A 108.4 . . ? C7A C8A H8A1 109.5 . . ? C7A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C7A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? O2A C9A O3A 126.0(2) . . ? O2A C9A N1A 124.5(2) . . ? O3A C9A N1A 109.5(2) . . ? O3A C10A C11A 101.9(2) . . ? O3A C10A C13A 109.9(3) . . ? C11A C10A C13A 110.0(3) . . ? O3A C10A C12A 110.6(2) . . ? C11A C10A C12A 111.6(3) . . ? C13A C10A C12A 112.3(3) . . ? C10A C11A H11A 109.5 . . ? C10A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C10A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C10A C12A H12A 109.5 . . ? C10A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C10A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C10A C13A H13A 109.5 . . ? C10A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C10A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C5B O1B C6B 120.6(2) . . ? C9B O3B C10B 122.23(19) . . ? C9B N1B C7B 121.8(2) . . ? C9B N1B H1B 119.1 . . ? C7B N1B H1B 119.1 . . ? C4B C1B H1B1 109.5 . . ? C4B C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C4B C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? C4B C2B H2B1 109.5 . . ? C4B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C4B C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C4B C3B H3B1 109.5 . . ? C4B C3B H3B2 109.5 . . ? H3B1 C3B H3B2 109.5 . . ? C4B C3B H3B3 109.5 . . ? H3B1 C3B H3B3 109.5 . . ? H3B2 C3B H3B3 109.5 . . ? C5B C4B C2B 112.4(3) . . ? C5B C4B C1B 106.9(3) . . ? C2B C4B C1B 108.6(3) . . ? C5B C4B C3B 108.8(2) . . ? C2B C4B C3B 108.7(3) . . ? C1B C4B C3B 111.5(3) . . ? O1B C5B C4B 110.6(3) . . ? O1B C5B S1B 123.9(2) . . ? C4B C5B S1B 125.4(2) . . ? O1B C6B C7B 107.4(2) . . ? O1B C6B H6B1 110.2 . . ? C7B C6B H6B1 110.2 . . ? O1B C6B H6B2 110.2 . . ? C7B C6B H6B2 110.2 . . ? H6B1 C6B H6B2 108.5 . . ? N1B C7B C6B 108.9(2) . . ? N1B C7B C8B 109.7(2) . . ? C6B C7B C8B 114.0(3) . . ? N1B C7B H7B 108.0 . . ? C6B C7B H7B 108.0 . . ? C8B C7B H7B 108.0 . . ? C7B C8B H8B1 109.5 . . ? C7B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C7B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? O2B C9B O3B 125.9(2) . . ? O2B C9B N1B 124.1(2) . . ? O3B C9B N1B 110.0(2) . . ? O3B C10B C13B 110.6(2) . . ? O3B C10B C11B 102.9(2) . . ? C13B C10B C11B 110.6(3) . . ? O3B C10B C12B 109.4(2) . . ? C13B C10B C12B 112.5(3) . . ? C11B C10B C12B 110.5(3) . . ? C10B C11B H11D 109.5 . . ? C10B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C10B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C10B C12B H12D 109.5 . . ? C10B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C10B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C10B C13B H13D 109.5 . . ? C10B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C10B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.526 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.060 _vrf_SYMMS02_compound35 ; PROBLEM: All angles should not be 90 for a monoclinic cell RESPONSE: This is rare, but beta angle is 90 in this case and structure is twinned TWIN 1 0 0 0 -1 0 0 0 -1 and BASF 0.40879 ; _vrf_PLAT220_compound35 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.29 Ratio RESPONSE: Structure contains four tert-butyl groups, and outer carbons often show larger U values due to small degree of disorder in their orientation ; _database_code_depnum_ccdc_archive 'CCDC 920886' ####################################################################### # # 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_compound36 #TrackingRef '17034_web_deposit_cif_file_0_JohnWallis_1358639628.WALLIS_CIFFILES.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-Dimethyl-O-((N'-Boc)-2-aminopropyl) thionocarbamate compound 36 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H22 N2 O3 S' _chemical_formula_weight 262.37 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.1321(4) _cell_length_b 11.0452(3) _cell_length_c 10.1525(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.532(3) _cell_angle_gamma 90.00 _cell_volume 1447.78(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7411 _cell_measurement_theta_min 2.9733 _cell_measurement_theta_max 29.3855 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 15.9832 _diffrn_reflns_number 13572 _diffrn_measurement_method '\w scans' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 29.46 _reflns_number_total 3569 _reflns_number_gt 2818 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0645P)^2^+0.1260P] 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 3569 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1132 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.008 _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 S1 S 0.06821(3) 0.48183(4) 0.22000(4) 0.03813(14) Uani 1 1 d . . . O1 O 0.15076(8) 0.38878(9) 0.45865(9) 0.0307(2) Uani 1 1 d . . . O2 O 0.35899(7) 0.27583(9) 0.73088(9) 0.0286(2) Uani 1 1 d . . . O3 O 0.47886(7) 0.32609(9) 0.60365(9) 0.0303(2) Uani 1 1 d . . . N1 N 0.11897(9) 0.58411(11) 0.46151(12) 0.0318(3) Uani 1 1 d . . . N2 N 0.33268(8) 0.24237(10) 0.50652(10) 0.0237(2) Uani 1 1 d . . . H2 H 0.3615 0.2463 0.4349 0.035(4) Uiso 1 1 calc R . . C1 C 0.16419(13) 0.57932(15) 0.60467(14) 0.0385(4) Uani 1 1 d . . . H1A H 0.1191 0.5319 0.6520 0.058 Uiso 1 1 calc R . . H1B H 0.1711 0.6617 0.6411 0.058 Uiso 1 1 calc R . . H1C H 0.2326 0.5412 0.6165 0.058 Uiso 1 1 calc R . . C2 C 0.08066(15) 0.70056(15) 0.40581(18) 0.0485(4) Uani 1 1 d . . . H2A H 0.1290 0.7337 0.3521 0.073 Uiso 1 1 calc R . . H2B H 0.0748 0.7566 0.4789 0.073 Uiso 1 1 calc R . . H2C H 0.0125 0.6897 0.3490 0.073 Uiso 1 1 calc R . . C3 C 0.11374(10) 0.48520(13) 0.38479(15) 0.0290(3) Uani 1 1 d . . . C4 C 0.15402(11) 0.27209(13) 0.39573(13) 0.0290(3) Uani 1 1 d . . . H4A H 0.1788 0.2805 0.3098 0.035 Uiso 1 1 calc R . . H4B H 0.0841 0.2352 0.3777 0.035 Uiso 1 1 calc R . . C5 C 0.22795(10) 0.19385(12) 0.49206(12) 0.0242(3) Uani 1 1 d . . . H5 H 0.2063 0.1951 0.5815 0.029 Uiso 1 1 calc R . . C6 C 0.22390(12) 0.06404(13) 0.44119(14) 0.0329(3) Uani 1 1 d . . . H6A H 0.2485 0.0613 0.3558 0.049 Uiso 1 1 calc R . . H6B H 0.1524 0.0344 0.4282 0.049 Uiso 1 1 calc R . . H6C H 0.2682 0.0128 0.5068 0.049 Uiso 1 1 calc R . . C7 C 0.38723(9) 0.28133(11) 0.62335(12) 0.0198(3) Uani 1 1 d . . . C8 C 0.55208(10) 0.38381(12) 0.71350(13) 0.0269(3) Uani 1 1 d . . . C9 C 0.49956(14) 0.48609(14) 0.7739(2) 0.0515(5) Uani 1 1 d . . . H9A H 0.4629 0.5378 0.7022 0.077 Uiso 1 1 calc R . . H9B H 0.5517 0.5341 0.8330 0.077 Uiso 1 1 calc R . . H9C H 0.4500 0.4527 0.8257 0.077 Uiso 1 1 calc R . . C10 C 0.59658(13) 0.29059(14) 0.81582(17) 0.0409(4) Uani 1 1 d . . . H10A H 0.5423 0.2617 0.8627 0.061 Uiso 1 1 calc R . . H10B H 0.6528 0.3269 0.8805 0.061 Uiso 1 1 calc R . . H10C H 0.6236 0.2224 0.7709 0.061 Uiso 1 1 calc R . . C11 C 0.63485(14) 0.4325(2) 0.64136(18) 0.0593(6) Uani 1 1 d . . . H11A H 0.6653 0.3655 0.5986 0.089 Uiso 1 1 calc R . . H11B H 0.6889 0.4726 0.7059 0.089 Uiso 1 1 calc R . . H11C H 0.6038 0.4908 0.5730 0.089 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 S1 0.0312(2) 0.0541(3) 0.0264(2) 0.00630(16) -0.00178(15) 0.00874(16) O1 0.0314(5) 0.0353(5) 0.0242(5) 0.0019(4) 0.0018(4) 0.0057(4) O2 0.0279(5) 0.0417(6) 0.0164(4) -0.0028(4) 0.0048(4) -0.0075(4) O3 0.0217(5) 0.0482(6) 0.0203(5) -0.0020(4) 0.0022(4) -0.0128(4) N1 0.0291(7) 0.0364(7) 0.0304(6) 0.0035(5) 0.0069(5) 0.0041(5) N2 0.0183(6) 0.0380(6) 0.0148(5) -0.0017(4) 0.0028(4) -0.0043(4) C1 0.0413(9) 0.0435(9) 0.0307(8) -0.0037(7) 0.0061(7) -0.0006(7) C2 0.0558(11) 0.0396(9) 0.0502(10) 0.0083(8) 0.0101(8) 0.0098(8) C3 0.0164(7) 0.0416(8) 0.0295(7) 0.0060(6) 0.0054(5) 0.0026(5) C4 0.0240(7) 0.0386(8) 0.0227(7) -0.0021(6) -0.0003(5) 0.0006(6) C5 0.0194(7) 0.0340(7) 0.0185(6) -0.0003(5) 0.0015(5) -0.0049(5) C6 0.0324(8) 0.0333(8) 0.0303(8) 0.0004(6) -0.0011(6) -0.0050(6) C7 0.0197(6) 0.0205(6) 0.0188(6) 0.0006(5) 0.0024(5) 0.0004(5) C8 0.0228(7) 0.0299(7) 0.0252(7) 0.0009(5) -0.0036(5) -0.0075(5) C9 0.0430(10) 0.0283(8) 0.0751(14) -0.0146(8) -0.0108(9) -0.0003(7) C10 0.0337(9) 0.0321(8) 0.0485(9) 0.0073(7) -0.0145(7) -0.0055(6) C11 0.0388(10) 0.0925(15) 0.0440(10) 0.0073(10) 0.0008(8) -0.0365(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 S1 C3 1.6710(15) . ? O1 C3 1.3415(17) . ? O1 C4 1.4427(17) . ? O2 C7 1.2169(15) . ? O3 C7 1.3492(15) . ? O3 C8 1.4774(15) . ? N1 C3 1.3362(19) . ? N1 C2 1.457(2) . ? N1 C1 1.4671(18) . ? N2 C7 1.3397(16) . ? N2 C5 1.4582(16) . ? C4 C5 1.5161(18) . ? C5 C6 1.522(2) . ? C8 C10 1.5030(19) . ? C8 C9 1.511(2) . ? C8 C11 1.516(2) . ? 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 C3 O1 C4 119.92(11) . . ? C7 O3 C8 121.41(10) . . ? C3 N1 C2 121.21(13) . . ? C3 N1 C1 121.09(12) . . ? C2 N1 C1 117.70(13) . . ? C7 N2 C5 123.30(11) . . ? N1 C3 O1 110.39(12) . . ? N1 C3 S1 124.94(11) . . ? O1 C3 S1 124.67(11) . . ? O1 C4 C5 106.91(10) . . ? N2 C5 C4 109.66(11) . . ? N2 C5 C6 110.75(11) . . ? C4 C5 C6 109.85(11) . . ? O2 C7 N2 125.23(12) . . ? O2 C7 O3 125.28(11) . . ? N2 C7 O3 109.48(10) . . ? O3 C8 C10 110.08(11) . . ? O3 C8 C9 110.29(12) . . ? C10 C8 C9 112.35(14) . . ? O3 C8 C11 102.33(11) . . ? C10 C8 C11 110.75(14) . . ? C9 C8 C11 110.60(15) . . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.252 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 920887' ####################################################################### # # 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_compound37 #TrackingRef '17034_web_deposit_cif_file_0_JohnWallis_1358639628.WALLIS_CIFFILES.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-Dimethyl-O-((N',N'-di-Boc)-2-aminopropyl) thionocarbamate compound 37 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H30 N2 O5 S' _chemical_formula_weight 362.48 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 5.9611(2) _cell_length_b 19.2487(6) _cell_length_c 17.6222(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.909(3) _cell_angle_gamma 90.00 _cell_volume 2014.61(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4960 _cell_measurement_theta_min 3.1686 _cell_measurement_theta_max 29.3468 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 15.9832 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8768 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 29.41 _reflns_number_total 4616 _reflns_number_gt 3514 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0589P)^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 4616 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 S1 S 0.86615(6) 0.03806(2) 0.34149(2) 0.03091(12) Uani 1 1 d . . . O1 O 1.17324(16) 0.12741(5) 0.40131(5) 0.0238(2) Uani 1 1 d . . . O2 O 1.08084(18) 0.26417(5) 0.27093(6) 0.0312(3) Uani 1 1 d . . . O3 O 1.22572(16) 0.35903(5) 0.33124(6) 0.0251(2) Uani 1 1 d . . . O4 O 1.61609(19) 0.23418(6) 0.46697(7) 0.0399(3) Uani 1 1 d . . . O5 O 1.36840(16) 0.32258(5) 0.46559(5) 0.0229(2) Uani 1 1 d . . . N1 N 0.92563(19) 0.09485(6) 0.48048(7) 0.0261(3) Uani 1 1 d . . . N2 N 1.37249(18) 0.25245(6) 0.36226(6) 0.0186(3) Uani 1 1 d . . . C1 C 0.7244(3) 0.06028(9) 0.50313(10) 0.0349(4) Uani 1 1 d . . . H1A H 0.5999 0.0936 0.5016 0.052 Uiso 1 1 calc R . . H1B H 0.7537 0.0421 0.5550 0.052 Uiso 1 1 calc R . . H1C H 0.6844 0.0219 0.4680 0.052 Uiso 1 1 calc R . . C2 C 1.0392(3) 0.14171(9) 0.53695(9) 0.0320(4) Uani 1 1 d . . . H2A H 1.1897 0.1528 0.5221 0.048 Uiso 1 1 calc R . . H2B H 1.0524 0.1191 0.5869 0.048 Uiso 1 1 calc R . . H2C H 0.9515 0.1846 0.5396 0.048 Uiso 1 1 calc R . . C3 C 0.9899(2) 0.08893(7) 0.41026(8) 0.0220(3) Uani 1 1 d . . . C4 C 1.2571(2) 0.13039(7) 0.32677(8) 0.0233(3) Uani 1 1 d . . . H4A H 1.1343 0.1430 0.2878 0.028 Uiso 1 1 calc R . . H4B H 1.3183 0.0846 0.3133 0.028 Uiso 1 1 calc R . . C5 C 1.4405(2) 0.18482(7) 0.33019(8) 0.0205(3) Uani 1 1 d . . . H5 H 1.5680 0.1666 0.3651 0.025 Uiso 1 1 calc R . . C6 C 1.5290(3) 0.19337(8) 0.25209(8) 0.0281(3) Uani 1 1 d . . . H6A H 1.4079 0.2105 0.2158 0.042 Uiso 1 1 calc R . . H6B H 1.5822 0.1484 0.2347 0.042 Uiso 1 1 calc R . . H6C H 1.6538 0.2267 0.2556 0.042 Uiso 1 1 calc R . . C7 C 1.2092(2) 0.29135(7) 0.31788(8) 0.0203(3) Uani 1 1 d . . . C8 C 1.0650(2) 0.40725(7) 0.28912(8) 0.0244(3) Uani 1 1 d . . . C9 C 0.8247(3) 0.38959(10) 0.30412(11) 0.0434(5) Uani 1 1 d . . . H9A H 0.7798 0.3462 0.2780 0.065 Uiso 1 1 calc R . . H9B H 0.7243 0.4272 0.2851 0.065 Uiso 1 1 calc R . . H9C H 0.8150 0.3840 0.3590 0.065 Uiso 1 1 calc R . . C10 C 1.1042(3) 0.40641(9) 0.20559(9) 0.0336(4) Uani 1 1 d . . . H10A H 1.2643 0.4142 0.1998 0.050 Uiso 1 1 calc R . . H10B H 1.0150 0.4432 0.1791 0.050 Uiso 1 1 calc R . . H10C H 1.0587 0.3613 0.1837 0.050 Uiso 1 1 calc R . . C11 C 1.1335(3) 0.47667(8) 0.32450(10) 0.0430(5) Uani 1 1 d . . . H11A H 1.1156 0.4753 0.3792 0.065 Uiso 1 1 calc R . . H11B H 1.0379 0.5134 0.3006 0.065 Uiso 1 1 calc R . . H11C H 1.2912 0.4862 0.3165 0.065 Uiso 1 1 calc R . . C12 C 1.4665(2) 0.26848(7) 0.43564(8) 0.0218(3) Uani 1 1 d . . . C13 C 1.4565(2) 0.34934(8) 0.54113(8) 0.0253(3) Uani 1 1 d . . . C14 C 1.3155(3) 0.41414(10) 0.54926(10) 0.0405(4) Uani 1 1 d . . . H14A H 1.3427 0.4470 0.5086 0.061 Uiso 1 1 calc R . . H14B H 1.3571 0.4358 0.5988 0.061 Uiso 1 1 calc R . . H14C H 1.1557 0.4015 0.5457 0.061 Uiso 1 1 calc R . . C15 C 1.7020(3) 0.36866(10) 0.54102(10) 0.0396(4) Uani 1 1 d . . . H15A H 1.7908 0.3269 0.5329 0.059 Uiso 1 1 calc R . . H15B H 1.7539 0.3897 0.5901 0.059 Uiso 1 1 calc R . . H15C H 1.7207 0.4020 0.5000 0.059 Uiso 1 1 calc R . . C16 C 1.4138(4) 0.29633(11) 0.60178(10) 0.0509(5) Uani 1 1 d . . . H16A H 1.2534 0.2844 0.5981 0.076 Uiso 1 1 calc R . . H16B H 1.4577 0.3159 0.6522 0.076 Uiso 1 1 calc R . . H16C H 1.5026 0.2544 0.5942 0.076 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 S1 0.0283(2) 0.0247(2) 0.0389(2) -0.00654(17) -0.00164(17) -0.00602(17) O1 0.0240(5) 0.0233(5) 0.0243(5) -0.0020(4) 0.0036(4) -0.0072(4) O2 0.0323(6) 0.0257(6) 0.0327(6) -0.0049(5) -0.0144(5) 0.0005(5) O3 0.0340(6) 0.0162(5) 0.0233(5) 0.0013(4) -0.0088(4) 0.0012(4) O4 0.0450(7) 0.0330(7) 0.0375(7) -0.0086(5) -0.0206(6) 0.0167(5) O5 0.0252(5) 0.0256(6) 0.0170(5) -0.0050(4) -0.0032(4) 0.0035(4) N1 0.0230(6) 0.0243(7) 0.0314(7) 0.0003(5) 0.0048(5) -0.0038(5) N2 0.0212(6) 0.0159(6) 0.0181(6) -0.0012(4) -0.0009(5) 0.0009(5) C1 0.0262(8) 0.0369(10) 0.0426(10) 0.0077(8) 0.0094(7) -0.0050(7) C2 0.0314(8) 0.0364(9) 0.0283(8) -0.0038(7) 0.0031(7) -0.0016(7) C3 0.0196(7) 0.0150(7) 0.0312(8) 0.0013(6) 0.0006(6) 0.0014(6) C4 0.0284(7) 0.0196(7) 0.0225(7) -0.0038(6) 0.0047(6) -0.0013(6) C5 0.0215(7) 0.0165(7) 0.0234(7) -0.0030(6) 0.0020(6) 0.0017(6) C6 0.0303(8) 0.0272(8) 0.0281(8) -0.0054(6) 0.0092(6) -0.0036(7) C7 0.0222(7) 0.0191(7) 0.0195(7) 0.0004(5) 0.0019(6) 0.0011(6) C8 0.0288(7) 0.0196(7) 0.0242(8) 0.0046(6) -0.0017(6) 0.0070(6) C9 0.0377(9) 0.0388(10) 0.0558(12) 0.0120(9) 0.0158(8) 0.0118(8) C10 0.0405(9) 0.0342(9) 0.0258(8) 0.0078(7) 0.0013(7) 0.0110(8) C11 0.0642(12) 0.0211(8) 0.0412(10) 0.0004(7) -0.0106(9) 0.0075(8) C12 0.0234(7) 0.0192(7) 0.0221(7) 0.0006(6) -0.0019(6) -0.0028(6) C13 0.0275(7) 0.0308(8) 0.0169(7) -0.0062(6) -0.0015(6) -0.0045(7) C14 0.0349(9) 0.0482(11) 0.0378(10) -0.0226(8) 0.0000(7) 0.0046(8) C15 0.0297(8) 0.0465(11) 0.0424(10) -0.0181(8) 0.0016(7) -0.0072(8) C16 0.0769(14) 0.0547(12) 0.0213(9) 0.0018(8) 0.0043(9) -0.0136(11) _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 S1 C3 1.6788(15) . ? O1 C3 1.3408(17) . ? O1 C4 1.4461(17) . ? O2 C7 1.1982(16) . ? O3 C7 1.3258(16) . ? O3 C8 1.4863(16) . ? O4 C12 1.2047(16) . ? O5 C12 1.3258(17) . ? O5 C13 1.4811(15) . ? N1 C3 1.3311(19) . ? N1 C1 1.4569(19) . ? N1 C2 1.4652(19) . ? N2 C12 1.3992(17) . ? N2 C7 1.4103(17) . ? N2 C5 1.4892(17) . ? C4 C5 1.511(2) . ? C5 C6 1.524(2) . ? C8 C10 1.510(2) . ? C8 C11 1.516(2) . ? C8 C9 1.517(2) . ? C13 C15 1.510(2) . ? C13 C16 1.515(2) . ? C13 C14 1.518(2) . ? 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 C3 O1 C4 118.52(11) . . ? C7 O3 C8 119.35(10) . . ? C12 O5 C13 119.76(10) . . ? C3 N1 C1 121.65(13) . . ? C3 N1 C2 122.08(12) . . ? C1 N1 C2 116.00(13) . . ? C12 N2 C7 126.75(12) . . ? C12 N2 C5 116.29(11) . . ? C7 N2 C5 116.81(10) . . ? N1 C3 O1 111.37(12) . . ? N1 C3 S1 125.27(11) . . ? O1 C3 S1 123.33(11) . . ? O1 C4 C5 107.24(11) . . ? N2 C5 C4 113.69(11) . . ? N2 C5 C6 112.00(11) . . ? C4 C5 C6 110.11(11) . . ? O2 C7 O3 125.79(12) . . ? O2 C7 N2 121.38(13) . . ? O3 C7 N2 112.71(11) . . ? O3 C8 C10 109.46(12) . . ? O3 C8 C11 101.87(11) . . ? C10 C8 C11 110.59(14) . . ? O3 C8 C9 110.54(12) . . ? C10 C8 C9 113.25(13) . . ? C11 C8 C9 110.55(14) . . ? O4 C12 O5 125.62(13) . . ? O4 C12 N2 121.67(13) . . ? O5 C12 N2 112.68(11) . . ? O5 C13 C15 110.72(12) . . ? O5 C13 C16 109.37(12) . . ? C15 C13 C16 112.85(15) . . ? O5 C13 C14 102.36(11) . . ? C15 C13 C14 110.02(13) . . ? C16 C13 C14 111.04(15) . . ? _diffrn_measured_fraction_theta_max 0.828 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.284 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 920888'