# Electronic Supplementary Material (ESI) for Green Chemistry # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N2 O S2' _chemical_formula_weight 244.37 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.7382(3) _cell_length_b 10.2853(3) _cell_length_c 11.9959(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.8370(10) _cell_angle_gamma 90.00 _cell_volume 1202.35(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4446 _cell_measurement_theta_min 2.725 _cell_measurement_theta_max 30.858 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.419 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.2000 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10607 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2125 _reflns_number_gt 1916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.7546P] 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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2125 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.96173(6) 0.13767(5) 0.21609(5) 0.03446(18) Uani 1 1 d . . . S2 S 0.94666(6) 0.31704(5) 0.01311(5) 0.03520(18) Uani 1 1 d . . . O1 O 0.83619(14) 0.08280(14) -0.01105(12) 0.0316(3) Uani 1 1 d . . . N2 N 0.60361(16) -0.06114(16) -0.16750(14) 0.0274(4) Uani 1 1 d . . . C1 C 0.91254(19) 0.17763(19) 0.06715(18) 0.0261(4) Uani 1 1 d . . . C6 C 0.6006(2) -0.16275(19) -0.09824(17) 0.0261(4) Uani 1 1 d . . . N1 N 0.47721(17) -0.16014(16) -0.09459(15) 0.0271(4) Uani 1 1 d . . . C5 C 0.4031(2) -0.0558(2) -0.16155(19) 0.0314(5) Uani 1 1 d . . . H5A H 0.3148 -0.0326 -0.1732 0.038 Uiso 1 1 calc R . . C2 C 0.7823(2) 0.1032(2) -0.14188(18) 0.0337(5) Uani 1 1 d . . . H2A H 0.8555 0.1258 -0.1656 0.040 Uiso 1 1 calc R . . H2B H 0.7153 0.1730 -0.1668 0.040 Uiso 1 1 calc R . . C4 C 0.4813(2) 0.0062(2) -0.20691(18) 0.0322(5) Uani 1 1 d . . . H4A H 0.4577 0.0805 -0.2557 0.039 Uiso 1 1 calc R . . C7 C 0.7168(2) -0.2539(2) -0.03159(19) 0.0319(5) Uani 1 1 d . . . H7A H 0.7818 -0.2435 -0.0688 0.038 Uiso 1 1 calc R . . C3 C 0.7159(2) -0.0233(2) -0.20086(19) 0.0349(5) Uani 1 1 d . . . H3A H 0.6801 -0.0148 -0.2894 0.042 Uiso 1 1 calc R . . H3B H 0.7848 -0.0914 -0.1756 0.042 Uiso 1 1 calc R . . C8 C 0.7938(2) -0.2143(2) 0.1035(2) 0.0388(5) Uani 1 1 d . . . H8A H 0.8177 -0.1238 0.1083 0.058 Uiso 1 1 calc R . . H8B H 0.8758 -0.2654 0.1412 0.058 Uiso 1 1 calc R . . H8C H 0.7361 -0.2287 0.1455 0.058 Uiso 1 1 calc R . . C9 C 0.6776(3) -0.3976(2) -0.0439(3) 0.0494(6) Uani 1 1 d . . . H9A H 0.6300 -0.4196 -0.1293 0.074 Uiso 1 1 calc R . . H9B H 0.6190 -0.4139 -0.0031 0.074 Uiso 1 1 calc R . . H9C H 0.7591 -0.4496 -0.0071 0.074 Uiso 1 1 calc R . . C10 C 0.4217(2) -0.2531(2) -0.0349(2) 0.0421(6) Uani 1 1 d . . . H10A H 0.4895 -0.3181 0.0068 0.063 Uiso 1 1 calc R . . H10B H 0.3415 -0.2939 -0.0957 0.063 Uiso 1 1 calc R . . H10C H 0.3975 -0.2083 0.0234 0.063 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 0.0380(3) 0.0353(3) 0.0241(3) -0.0019(2) 0.0071(2) -0.0005(2) S2 0.0387(3) 0.0297(3) 0.0359(3) -0.0007(2) 0.0143(3) -0.0052(2) O1 0.0368(8) 0.0317(8) 0.0229(7) -0.0024(6) 0.0094(6) -0.0088(6) N2 0.0284(9) 0.0290(9) 0.0230(8) -0.0026(7) 0.0090(7) -0.0049(7) C1 0.0194(9) 0.0288(10) 0.0288(10) -0.0040(8) 0.0090(8) 0.0016(7) C6 0.0276(10) 0.0280(10) 0.0220(10) -0.0036(8) 0.0098(8) -0.0003(8) N1 0.0272(9) 0.0289(9) 0.0253(9) 0.0017(7) 0.0110(7) 0.0011(7) C5 0.0260(10) 0.0287(11) 0.0334(11) -0.0020(8) 0.0067(9) 0.0033(8) C2 0.0361(11) 0.0407(12) 0.0232(10) -0.0010(9) 0.0114(9) -0.0115(9) C4 0.0332(11) 0.0266(11) 0.0285(11) 0.0028(8) 0.0047(9) 0.0008(8) C7 0.0305(10) 0.0327(11) 0.0315(11) -0.0004(9) 0.0122(9) 0.0062(8) C3 0.0373(11) 0.0455(13) 0.0265(11) -0.0074(9) 0.0178(9) -0.0119(10) C8 0.0378(12) 0.0355(12) 0.0332(12) 0.0042(9) 0.0053(10) 0.0068(10) C9 0.0489(14) 0.0338(13) 0.0571(16) -0.0094(11) 0.0138(12) 0.0095(11) C10 0.0384(12) 0.0463(14) 0.0474(14) 0.0134(11) 0.0238(11) 0.0018(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 C1 1.687(2) . ? S2 C1 1.676(2) . ? O1 C1 1.363(2) . ? O1 C2 1.442(2) . ? N2 C6 1.344(3) . ? N2 C4 1.381(3) . ? N2 C3 1.473(2) . ? C6 N1 1.344(3) . ? C6 C7 1.496(3) . ? N1 C5 1.376(3) . ? N1 C10 1.463(3) . ? C5 C4 1.338(3) . ? C5 H5A 0.9300 . ? C2 C3 1.509(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C4 H4A 0.9300 . ? C7 C9 1.527(3) . ? C7 C8 1.533(3) . ? C7 H7A 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 119.69(16) . . ? C6 N2 C4 109.60(16) . . ? C6 N2 C3 127.47(18) . . ? C4 N2 C3 122.93(17) . . ? O1 C1 S2 120.80(15) . . ? O1 C1 S1 112.63(14) . . ? S2 C1 S1 126.56(12) . . ? N2 C6 N1 106.52(17) . . ? N2 C6 C7 125.94(17) . . ? N1 C6 C7 127.40(18) . . ? C6 N1 C5 109.43(17) . . ? C6 N1 C10 127.79(17) . . ? C5 N1 C10 122.74(17) . . ? C4 C5 N1 107.56(18) . . ? C4 C5 H5A 126.2 . . ? N1 C5 H5A 126.2 . . ? O1 C2 C3 106.21(17) . . ? O1 C2 H2A 110.5 . . ? C3 C2 H2A 110.5 . . ? O1 C2 H2B 110.5 . . ? C3 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? C5 C4 N2 106.88(18) . . ? C5 C4 H4A 126.6 . . ? N2 C4 H4A 126.6 . . ? C6 C7 C9 114.89(18) . . ? C6 C7 C8 110.90(17) . . ? C9 C7 C8 111.36(19) . . ? C6 C7 H7A 106.4 . . ? C9 C7 H7A 106.4 . . ? C8 C7 H7A 106.4 . . ? N2 C3 C2 112.33(17) . . ? N2 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.459 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 971543' ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N2 O S2' _chemical_formula_weight 244.37 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.0242(4) _cell_length_b 15.4761(9) _cell_length_c 11.2508(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.0820(10) _cell_angle_gamma 90.00 _cell_volume 1222.24(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 891 _cell_measurement_theta_min 2.239 _cell_measurement_theta_max 25.381 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.413 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.2000 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6979 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0882 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2757 _reflns_number_gt 1683 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2757 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.01283(11) 0.80011(5) 0.61492(8) 0.0293(2) Uani 1 1 d . . . S2 S 0.33218(11) 0.91041(6) 0.71438(8) 0.0322(2) Uani 1 1 d . . . O1 O 0.0030(3) 0.96857(12) 0.65270(19) 0.0280(5) Uani 1 1 d . . . N1 N -0.1012(3) 1.14777(15) 0.9043(2) 0.0224(6) Uani 1 1 d . . . N2 N -0.2383(3) 1.09000(15) 0.7491(2) 0.0221(6) Uani 1 1 d . . . C4 C -0.3564(4) 1.07586(19) 0.8436(3) 0.0255(7) Uani 1 1 d . . . H4A H -0.4729 1.0472 0.8408 0.031 Uiso 1 1 calc R . . C3 C -0.2713(4) 1.05489(19) 0.6290(3) 0.0248(7) Uani 1 1 d . . . H3A H -0.2101 1.0920 0.5723 0.030 Uiso 1 1 calc R . . H3B H -0.4070 1.0550 0.6096 0.030 Uiso 1 1 calc R . . C6 C -0.0848(4) 1.13407(18) 0.7880(3) 0.0243(7) Uani 1 1 d . . . C1 C 0.1078(4) 0.8938(2) 0.6593(3) 0.0265(7) Uani 1 1 d . . . C7 C 0.0772(5) 1.1618(2) 0.7183(3) 0.0331(8) Uani 1 1 d . . . H7A H 0.1672 1.1924 0.7689 0.050 Uiso 1 1 calc R . . H7B H 0.0327 1.1990 0.6550 0.050 Uiso 1 1 calc R . . H7C H 0.1377 1.1120 0.6855 0.050 Uiso 1 1 calc R . . C2 C -0.1964(4) 0.96475(19) 0.6173(3) 0.0261(7) Uani 1 1 d . . . H2A H -0.2636 0.9256 0.6684 0.031 Uiso 1 1 calc R . . H2B H -0.2122 0.9448 0.5358 0.031 Uiso 1 1 calc R . . C5 C -0.2701(4) 1.11138(19) 0.9392(3) 0.0263(7) Uani 1 1 d . . . H5A H -0.3156 1.1116 1.0158 0.032 Uiso 1 1 calc R . . C8 C 0.0436(4) 1.1900(2) 0.9842(3) 0.0293(8) Uani 1 1 d . . . H8A H 0.1278 1.2240 0.9346 0.035 Uiso 1 1 calc R . . C10 C 0.1630(5) 1.1214(2) 1.0468(3) 0.0391(9) Uani 1 1 d . . . H10A H 0.2198 1.0850 0.9888 0.059 Uiso 1 1 calc R . . H10B H 0.0838 1.0872 1.0962 0.059 Uiso 1 1 calc R . . H10C H 0.2614 1.1485 1.0951 0.059 Uiso 1 1 calc R . . C9 C -0.0496(5) 1.2513(2) 1.0683(3) 0.0347(8) Uani 1 1 d . . . H9A H -0.1229 1.2932 1.0235 0.052 Uiso 1 1 calc R . . H9B H 0.0465 1.2801 1.1164 0.052 Uiso 1 1 calc R . . H9C H -0.1321 1.2195 1.1186 0.052 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 0.0301(4) 0.0258(4) 0.0317(5) -0.0035(4) -0.0036(4) -0.0022(3) S2 0.0231(4) 0.0372(5) 0.0358(5) -0.0008(4) -0.0032(4) -0.0063(4) O1 0.0225(11) 0.0256(12) 0.0360(14) -0.0050(10) 0.0023(10) -0.0008(9) N1 0.0242(13) 0.0212(13) 0.0215(15) -0.0003(11) -0.0021(11) 0.0005(11) N2 0.0244(13) 0.0203(13) 0.0217(15) -0.0022(11) -0.0002(11) 0.0021(11) C4 0.0233(15) 0.0245(16) 0.0290(19) -0.0023(14) 0.0046(14) -0.0003(13) C3 0.0289(17) 0.0278(17) 0.0177(18) -0.0030(14) -0.0010(14) -0.0013(13) C6 0.0288(17) 0.0176(15) 0.0264(19) -0.0009(13) -0.0003(14) -0.0008(13) C1 0.0241(16) 0.0330(18) 0.0229(19) 0.0021(14) 0.0067(14) 0.0003(13) C7 0.0364(19) 0.0356(19) 0.028(2) -0.0002(16) 0.0049(16) -0.0136(15) C2 0.0245(16) 0.0293(18) 0.0244(19) -0.0061(14) 0.0012(14) -0.0043(13) C5 0.0298(17) 0.0264(17) 0.0229(19) -0.0005(14) 0.0049(15) -0.0013(13) C8 0.0271(17) 0.0323(18) 0.028(2) -0.0011(15) -0.0045(15) -0.0022(14) C10 0.037(2) 0.043(2) 0.036(2) -0.0032(17) -0.0069(17) 0.0082(16) C9 0.0390(19) 0.0294(19) 0.036(2) -0.0087(16) -0.0034(16) 0.0012(15) _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 1.665(3) . ? S2 C1 1.692(3) . ? O1 C1 1.372(3) . ? O1 C2 1.444(3) . ? N1 C6 1.334(4) . ? N1 C5 1.383(4) . ? N1 C8 1.485(4) . ? N2 C6 1.336(4) . ? N2 C4 1.390(4) . ? N2 C3 1.468(4) . ? C4 C5 1.333(4) . ? C4 H4A 0.9300 . ? C3 C2 1.498(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C6 C7 1.469(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C5 H5A 0.9300 . ? C8 C9 1.506(4) . ? C8 C10 1.511(4) . ? C8 H8A 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 119.6(2) . . ? C6 N1 C5 108.6(2) . . ? C6 N1 C8 125.6(3) . . ? C5 N1 C8 125.7(3) . . ? C6 N2 C4 109.1(3) . . ? C6 N2 C3 126.1(3) . . ? C4 N2 C3 124.6(3) . . ? C5 C4 N2 106.6(3) . . ? C5 C4 H4A 126.7 . . ? N2 C4 H4A 126.7 . . ? N2 C3 C2 112.4(2) . . ? N2 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? N1 C6 N2 107.8(3) . . ? N1 C6 C7 125.0(3) . . ? N2 C6 C7 127.2(3) . . ? O1 C1 S1 120.6(2) . . ? O1 C1 S2 112.5(2) . . ? S1 C1 S2 126.88(19) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C2 C3 106.1(2) . . ? O1 C2 H2A 110.5 . . ? C3 C2 H2A 110.5 . . ? O1 C2 H2B 110.5 . . ? C3 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? C4 C5 N1 108.0(3) . . ? C4 C5 H5A 126.0 . . ? N1 C5 H5A 126.0 . . ? N1 C8 C9 110.7(2) . . ? N1 C8 C10 109.2(2) . . ? C9 C8 C10 113.3(3) . . ? N1 C8 H8A 107.8 . . ? C9 C8 H8A 107.8 . . ? C10 C8 H8A 107.8 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.440 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 971544' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H19 N2 O5' _chemical_formula_weight 247.27 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 'Pbcn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.1669(7) _cell_length_b 12.0650(7) _cell_length_c 19.2806(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2830.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3172 _cell_measurement_theta_min 2.378 _cell_measurement_theta_max 23.492 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.2000 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14862 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2498 _reflns_number_gt 1905 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.4111P)^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 contr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2498 _refine_ls_number_parameters 151 _refine_ls_number_restraints 150 _refine_ls_R_factor_all 0.1244 _refine_ls_R_factor_gt 0.1080 _refine_ls_wR_factor_ref 0.4047 _refine_ls_wR_factor_gt 0.3651 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 1.027 _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 O4 O 0.3997(2) 0.0976(2) 0.63965(13) 0.0559(10) Uani 1 1 d . . . O3 O 0.5262(2) 0.0973(2) 0.55669(14) 0.0618(10) Uani 1 1 d . . . C1 C 0.4417(3) 0.0598(3) 0.58570(16) 0.0395(10) Uani 1 1 d . . . O2 O 0.3931(2) -0.0275(2) 0.55732(15) 0.0653(11) Uani 1 1 d . . . H2C H 0.4260 -0.0441 0.5198 0.098 Uiso 1 1 d R . . N2 N 0.7709(3) 0.1829(2) 0.25261(15) 0.0455(10) Uani 1 1 d . . . C4 C 0.8547(3) 0.2527(3) 0.23044(18) 0.0460(10) Uani 1 1 d U . . H4A H 0.8986 0.3002 0.2592 0.055 Uiso 1 1 d R . . N1 N 0.7850(3) 0.1637(3) 0.14234(16) 0.0640(12) Uani 1 1 d . . . O1 O 0.8051(3) -0.0154(3) 0.33952(18) 0.0745(12) Uani 1 1 d . . . H1A H 0.7402 -0.0388 0.3467 0.112 Uiso 1 1 d R . . C6 C 0.7292(4) 0.1303(3) 0.19808(18) 0.0562(12) Uani 1 1 d U . . C5 C 0.8633(3) 0.2408(3) 0.16137(19) 0.0551(12) Uani 1 1 d U . . H5C H 0.9135 0.2786 0.1311 0.066 Uiso 1 1 d R . . C2 C 0.8138(4) 0.0951(4) 0.3636(2) 0.0606(12) Uani 1 1 d U . . H2A H 0.8884 0.1196 0.3581 0.073 Uiso 1 1 d R . . H2B H 0.7966 0.0970 0.4122 0.073 Uiso 1 1 d R . . C3 C 0.7392(3) 0.1718(3) 0.32575(19) 0.0491(11) Uani 1 1 d U . . H3A H 0.6651 0.1448 0.3286 0.059 Uiso 1 1 d R . . H3B H 0.7417 0.2432 0.3476 0.059 Uiso 1 1 d R . . C7 C 0.6318(5) 0.0527(5) 0.1994(3) 0.0860(18) Uani 1 1 d U . . H7A H 0.6056 0.0436 0.2460 0.129 Uiso 1 1 d R . . H7B H 0.5733 0.0799 0.1707 0.129 Uiso 1 1 d R . . H7C H 0.6568 -0.0174 0.1820 0.129 Uiso 1 1 d R . . C8 C 0.7595(6) 0.1333(5) 0.0690(2) 0.101(2) Uani 1 1 d U . . H8A H 0.7088 0.0723 0.0694 0.122 Uiso 1 1 d R . . C9 C 0.7089(9) 0.2285(7) 0.0326(4) 0.158(4) Uani 1 1 d U . . H9B H 0.6917 0.2114 -0.0148 0.237 Uiso 1 1 d R . . H9A H 0.6425 0.2455 0.0573 0.237 Uiso 1 1 d R . . H9C H 0.7574 0.2912 0.0342 0.237 Uiso 1 1 d R . . C10 C 0.8621(11) 0.1000(10) 0.0347(4) 0.195(5) Uani 1 1 d U . . H10A H 0.8933 0.0373 0.0582 0.293 Uiso 1 1 d R . . H10B H 0.8450 0.0800 -0.0123 0.293 Uiso 1 1 d R . . H10C H 0.9140 0.1599 0.0348 0.293 Uiso 1 1 d R . . O5 O 1.0000 0.1454(16) 0.7500 0.271(7) Uani 1 2 d SU . . H5B H 1.0334 0.2065 0.7563 0.326 Uiso 0.50 1 d PR . . H5A H 1.0424 0.0917 0.7598 0.407 Uiso 0.50 1 d PR . . 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 O4 0.075(2) 0.0566(17) 0.0365(16) -0.0129(11) 0.0102(12) -0.0014(13) O3 0.0702(19) 0.074(2) 0.0413(17) -0.0233(13) 0.0110(12) -0.0267(14) C1 0.0483(19) 0.0417(18) 0.0285(18) -0.0024(12) 0.0011(13) 0.0004(14) O2 0.085(2) 0.0610(19) 0.0503(19) -0.0240(12) 0.0298(14) -0.0315(14) N2 0.0553(18) 0.0482(18) 0.0329(17) 0.0031(12) -0.0011(12) -0.0195(13) C4 0.060(2) 0.0412(19) 0.037(2) -0.0027(14) -0.0024(15) -0.0189(15) N1 0.099(3) 0.062(2) 0.0321(18) 0.0027(13) -0.0098(16) -0.041(2) O1 0.077(2) 0.072(2) 0.075(2) 0.0155(16) 0.0240(15) 0.0141(16) C6 0.076(3) 0.052(2) 0.040(2) 0.0039(16) -0.0060(17) -0.0331(19) C5 0.078(3) 0.054(2) 0.034(2) 0.0038(15) -0.0008(16) -0.0282(19) C2 0.063(2) 0.077(3) 0.041(2) 0.0114(18) -0.0004(17) -0.012(2) C3 0.058(2) 0.050(2) 0.039(2) -0.0053(15) 0.0060(15) -0.0153(16) C7 0.104(4) 0.085(3) 0.069(3) 0.008(2) -0.009(2) -0.062(3) C8 0.161(5) 0.107(4) 0.037(2) 0.000(3) -0.008(3) -0.086(4) C9 0.260(9) 0.143(6) 0.072(4) 0.043(4) -0.085(5) -0.099(7) C10 0.251(10) 0.254(11) 0.081(5) -0.104(6) 0.054(6) -0.112(9) O5 0.217(9) 0.306(11) 0.291(11) 0.000 0.164(8) 0.000 _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 O4 C1 1.246(4) . ? O3 C1 1.255(4) . ? C1 O2 1.326(4) . ? O2 H2C 0.8501 . ? N2 C6 1.329(4) . ? N2 C4 1.389(4) . ? N2 C3 1.468(4) . ? C4 C5 1.343(5) . ? C4 H4A 0.9599 . ? N1 C6 1.334(5) . ? N1 C5 1.380(5) . ? N1 C8 1.493(5) . ? O1 C2 1.415(6) . ? O1 H1A 0.8499 . ? C6 C7 1.510(6) . ? C5 H5C 0.9601 . ? C2 C3 1.487(6) . ? C2 H2A 0.9600 . ? C2 H2B 0.9597 . ? C3 H3A 0.9599 . ? C3 H3B 0.9598 . ? C7 H7A 0.9599 . ? C7 H7B 0.9601 . ? C7 H7C 0.9598 . ? C8 C9 1.480(11) . ? C8 C10 1.470(14) . ? C8 H8A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9A 0.9600 . ? C9 H9C 0.9598 . ? C10 H10A 0.9600 . ? C10 H10B 0.9601 . ? C10 H10C 0.9600 . ? O5 H5B 0.8501 . ? O5 H5A 0.8500 . ? 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 O4 C1 O3 125.2(3) . . ? O4 C1 O2 116.9(3) . . ? O3 C1 O2 117.9(3) . . ? C1 O2 H2C 109.1 . . ? C6 N2 C4 109.0(3) . . ? C6 N2 C3 128.0(3) . . ? C4 N2 C3 122.9(3) . . ? C5 C4 N2 107.3(3) . . ? C5 C4 H4A 126.4 . . ? N2 C4 H4A 126.3 . . ? C6 N1 C5 109.9(3) . . ? C6 N1 C8 125.6(3) . . ? C5 N1 C8 124.1(3) . . ? C2 O1 H1A 109.2 . . ? N2 C6 N1 107.3(3) . . ? N2 C6 C7 125.6(4) . . ? N1 C6 C7 126.9(4) . . ? C4 C5 N1 106.4(3) . . ? C4 C5 H5C 127.0 . . ? N1 C5 H5C 126.6 . . ? O1 C2 C3 112.3(3) . . ? O1 C2 H2A 108.9 . . ? C3 C2 H2A 109.3 . . ? O1 C2 H2B 109.0 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 107.9 . . ? N2 C3 C2 111.6(3) . . ? N2 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? N2 C3 H3B 109.3 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 108.0 . . ? C6 C7 H7A 110.3 . . ? C6 C7 H7B 111.1 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 106.9 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C10 110.6(8) . . ? C9 C8 N1 110.2(6) . . ? C10 C8 N1 108.5(6) . . ? C9 C8 H8A 109.4 . . ? C10 C8 H8A 109.8 . . ? N1 C8 H8A 108.4 . . ? C8 C9 H9B 112.1 . . ? C8 C9 H9A 106.3 . . ? H9B C9 H9A 109.5 . . ? C8 C9 H9C 110.0 . . ? H9B C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? C8 C10 H10A 109.8 . . ? C8 C10 H10B 108.1 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 110.6 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? H5B O5 H5A 109.8 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.509 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 971545'