# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 #====================================================================== _audit_creation_method SHELXL-97 # SUBMISSION DETAILS _publ_contact_author_name G.Sekar _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology-Madras Chennai-600 036 India ; _publ_contact_author_email ; gsekar@iitm.ac.in ; _publ_contact_author_fax '91 44 2257 4202' _publ_contact_author_phone '91 44 2257 4229' #======================================================================= _publ_section_title ; Stereospecific chlorination of \b-substituted cyclic alcohols by using PPh~3~/NCS: factors that control the stereospecificity ; # TITLE AND AUTHOR LIST loop_ _publ_author_name _publ_author_address E.A.Jaseer ; Department of Chemistry Indian Institute of Technology-Madras Chennai-600 036 India ; 'Ajay B Naidu' ; Department of Chemistry Indian Institute of Technology-Madras Chennai-600 036 India ; 'Sreehari S Kumar' ; Department of Chemistry Indian Institute of Technology-Madras Chennai-600 036 India ; 'R.Koteshwar Rao' ; Department of Chemistry Indian Institute of Technology-Madras Chennai-600 036 India ; 'Krishna G.Thakur' ; Department of Chemistry Indian Institute of Technology-Madras Chennai-600 036 India ; ; G.Sekar ; ; Department of Chemistry Indian Institute of Technology-Madras Chennai-600 036 India ; #======================================================================= data_91a _database_code_depnum_ccdc_archive 'CCDC 621755' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 Cl N O2 S' _chemical_formula_sum 'C13 H18 Cl N O2 S' _chemical_formula_weight 287.79 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7769(4) _cell_length_b 9.7641(8) _cell_length_c 11.4462(8) _cell_angle_alpha 76.916(5) _cell_angle_beta 80.416(4) _cell_angle_gamma 74.897(4) _cell_volume 707.58(9) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3055 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 28.45 _exptl_crystal_description Prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8055 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker axs kappa apex2' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4438 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2382 _reflns_number_gt 1996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (WINGX)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP32 (WINGX)' _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^)+(0.0842P)^2^+1.0366P] 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 2382 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1733 _refine_ls_wR_factor_gt 0.1578 _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 C1 C 0.5530(5) 0.2457(4) 0.7551(3) 0.0407(8) Uani 1 1 d . . . H1 H 0.4147 0.3079 0.7479 0.049 Uiso 1 1 calc R . . C2 C 0.6679(6) 0.3142(5) 0.8207(4) 0.0517(10) Uani 1 1 d . . . H2A H 0.6037 0.3124 0.9032 0.062 Uiso 1 1 calc R . . H2B H 0.6586 0.4144 0.7815 0.062 Uiso 1 1 calc R . . C3 C 0.8949(7) 0.2342(5) 0.8213(4) 0.0581(11) Uani 1 1 d . . . H3A H 0.9662 0.2849 0.8579 0.070 Uiso 1 1 calc R . . H3B H 0.9048 0.1377 0.8696 0.070 Uiso 1 1 calc R . . C4 C 0.9971(6) 0.2238(6) 0.6944(4) 0.0609(12) Uani 1 1 d . . . H4A H 1.1380 0.1680 0.6981 0.073 Uiso 1 1 calc R . . H4B H 1.0006 0.3200 0.6489 0.073 Uiso 1 1 calc R . . C5 C 0.8843(5) 0.1528(5) 0.6296(4) 0.0478(10) Uani 1 1 d . . . H5A H 0.8939 0.0529 0.6697 0.057 Uiso 1 1 calc R . . H5B H 0.9484 0.1538 0.5471 0.057 Uiso 1 1 calc R . . C6 C 0.6579(5) 0.2329(4) 0.6292(3) 0.0332(7) Uani 1 1 d . . . H6 H 0.6543 0.3313 0.5837 0.040 Uiso 1 1 calc R . . C7 C 0.6671(5) 0.2769(4) 0.3309(3) 0.0350(8) Uani 1 1 d . . . C8 C 0.7703(6) 0.3807(4) 0.3331(3) 0.0427(9) Uani 1 1 d . . . H8 H 0.7243 0.4414 0.3889 0.051 Uiso 1 1 calc R . . C9 C 0.9427(6) 0.3938(4) 0.2516(4) 0.0479(9) Uani 1 1 d . . . H9 H 1.0148 0.4616 0.2547 0.057 Uiso 1 1 calc R . . C10 C 1.0100(6) 0.3073(4) 0.1649(4) 0.0459(9) Uani 1 1 d . . . C11 C 0.9038(6) 0.2069(5) 0.1630(4) 0.0525(10) Uani 1 1 d . . . H11 H 0.9472 0.1490 0.1051 0.063 Uiso 1 1 calc R . . C12 C 0.7316(6) 0.1888(4) 0.2458(4) 0.0441(9) Uani 1 1 d . . . H12 H 0.6618 0.1191 0.2438 0.053 Uiso 1 1 calc R . . C13 C 1.2006(7) 0.3233(6) 0.0774(5) 0.0670(13) Uani 1 1 d . . . H13A H 1.2326 0.2508 0.0285 0.101 Uiso 1 1 calc R . . H13B H 1.3140 0.3118 0.1218 0.101 Uiso 1 1 calc R . . H13C H 1.1757 0.4174 0.0266 0.101 Uiso 1 1 calc R . . N1 N 0.5472(4) 0.1667(3) 0.5659(3) 0.0371(7) Uani 1 1 d . . . H1 H 0.5301 0.0809 0.5960 0.045 Uiso 1 1 calc R . . O1 O 0.3576(4) 0.1576(3) 0.4063(3) 0.0446(7) Uani 1 1 d . . . O2 O 0.3430(4) 0.3939(3) 0.4581(3) 0.0460(7) Uani 1 1 d . . . S1 S 0.45718(12) 0.25188(9) 0.44094(8) 0.0341(3) Uani 1 1 d . . . Cl1 Cl 0.52715(17) 0.07159(12) 0.84262(10) 0.0581(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0327(17) 0.034(2) 0.052(2) -0.0083(16) -0.0021(15) -0.0044(14) C2 0.058(2) 0.048(2) 0.054(2) -0.0159(19) -0.0019(19) -0.0191(19) C3 0.057(2) 0.061(3) 0.065(3) -0.009(2) -0.025(2) -0.023(2) C4 0.035(2) 0.078(3) 0.073(3) -0.013(2) -0.0117(19) -0.019(2) C5 0.0291(18) 0.054(2) 0.059(2) -0.0162(19) -0.0014(16) -0.0051(16) C6 0.0293(16) 0.0263(18) 0.0439(19) -0.0059(14) -0.0060(13) -0.0060(13) C7 0.0297(16) 0.0273(18) 0.0447(19) -0.0072(14) -0.0086(14) 0.0023(13) C8 0.050(2) 0.0296(19) 0.050(2) -0.0142(16) -0.0007(16) -0.0081(16) C9 0.047(2) 0.040(2) 0.058(2) -0.0073(18) -0.0032(17) -0.0169(17) C10 0.0399(19) 0.042(2) 0.047(2) -0.0038(17) -0.0033(16) 0.0004(16) C11 0.054(2) 0.048(3) 0.052(2) -0.0198(19) -0.0019(18) 0.0015(19) C12 0.045(2) 0.036(2) 0.056(2) -0.0149(17) -0.0102(17) -0.0106(16) C13 0.048(2) 0.072(3) 0.071(3) -0.012(2) 0.008(2) -0.007(2) N1 0.0369(15) 0.0281(16) 0.0464(17) -0.0037(12) -0.0070(12) -0.0091(12) O1 0.0385(13) 0.0373(15) 0.0612(17) -0.0112(12) -0.0141(11) -0.0074(11) O2 0.0367(13) 0.0283(14) 0.0684(18) -0.0136(12) -0.0076(12) 0.0051(10) S1 0.0293(4) 0.0249(5) 0.0474(5) -0.0080(3) -0.0082(3) -0.0017(3) Cl1 0.0698(7) 0.0564(7) 0.0520(6) -0.0001(5) -0.0037(5) -0.0324(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.514(5) . ? C1 C2 1.521(6) . ? C1 Cl1 1.802(4) . ? C1 H1 0.9800 . ? C2 C3 1.534(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.515(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.521(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.530(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.467(4) . ? C6 H6 0.9800 . ? C7 C8 1.380(5) . ? C7 C12 1.386(5) . ? C7 S1 1.765(3) . ? C8 C9 1.383(5) . ? C8 H8 0.9300 . ? C9 C10 1.391(6) . ? C9 H9 0.9300 . ? C10 C11 1.364(6) . ? C10 C13 1.516(6) . ? C11 C12 1.398(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N1 S1 1.612(3) . ? N1 H1 0.8600 . ? O1 S1 1.427(3) . ? O2 S1 1.440(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 111.7(3) . . ? C6 C1 Cl1 111.0(3) . . ? C2 C1 Cl1 109.7(3) . . ? C6 C1 H1 108.1 . . ? C2 C1 H1 108.1 . . ? Cl1 C1 H1 108.1 . . ? C1 C2 C3 111.4(3) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 111.2(4) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 111.9(3) . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C6 110.5(3) . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C1 111.7(3) . . ? N1 C6 C5 111.2(3) . . ? C1 C6 C5 112.2(3) . . ? N1 C6 H6 107.1 . . ? C1 C6 H6 107.1 . . ? C5 C6 H6 107.1 . . ? C8 C7 C12 120.6(3) . . ? C8 C7 S1 119.6(3) . . ? C12 C7 S1 119.8(3) . . ? C7 C8 C9 119.4(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 121.2(4) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 118.4(4) . . ? C11 C10 C13 121.6(4) . . ? C9 C10 C13 119.9(4) . . ? C10 C11 C12 121.8(4) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C7 C12 C11 118.5(4) . . ? C7 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 N1 S1 121.1(2) . . ? C6 N1 H1 119.4 . . ? S1 N1 H1 119.4 . . ? O1 S1 O2 119.94(15) . . ? O1 S1 N1 106.08(16) . . ? O2 S1 N1 107.78(16) . . ? O1 S1 C7 108.10(17) . . ? O2 S1 C7 106.48(16) . . ? N1 S1 C7 107.99(15) . . ? 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 C6 C1 C2 C3 -53.8(4) . . . . ? Cl1 C1 C2 C3 69.8(4) . . . . ? C1 C2 C3 C4 54.5(5) . . . . ? C2 C3 C4 C5 -55.7(5) . . . . ? C3 C4 C5 C6 55.4(5) . . . . ? C2 C1 C6 N1 179.9(3) . . . . ? Cl1 C1 C6 N1 57.1(3) . . . . ? C2 C1 C6 C5 54.3(4) . . . . ? Cl1 C1 C6 C5 -68.6(3) . . . . ? C4 C5 C6 N1 179.4(3) . . . . ? C4 C5 C6 C1 -54.6(4) . . . . ? C12 C7 C8 C9 -1.8(5) . . . . ? S1 C7 C8 C9 175.9(3) . . . . ? C7 C8 C9 C10 2.1(6) . . . . ? C8 C9 C10 C11 -1.0(6) . . . . ? C8 C9 C10 C13 -179.5(4) . . . . ? C9 C10 C11 C12 -0.4(6) . . . . ? C13 C10 C11 C12 178.0(4) . . . . ? C8 C7 C12 C11 0.4(5) . . . . ? S1 C7 C12 C11 -177.3(3) . . . . ? C10 C11 C12 C7 0.7(6) . . . . ? C1 C6 N1 S1 120.2(3) . . . . ? C5 C6 N1 S1 -113.6(3) . . . . ? C6 N1 S1 O1 -179.1(2) . . . . ? C6 N1 S1 O2 -49.4(3) . . . . ? C6 N1 S1 C7 65.2(3) . . . . ? C8 C7 S1 O1 170.1(3) . . . . ? C12 C7 S1 O1 -12.2(3) . . . . ? C8 C7 S1 O2 40.0(3) . . . . ? C12 C7 S1 O2 -142.3(3) . . . . ? C8 C7 S1 N1 -75.5(3) . . . . ? C12 C7 S1 N1 102.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.573 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.085 #======================================================================= data_jaseer _database_code_depnum_ccdc_archive 'CCDC 621756' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 N O5' _chemical_formula_weight 293.31 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2564(6) _cell_length_b 7.4017(5) _cell_length_c 15.5988(13) _cell_angle_alpha 88.923(5) _cell_angle_beta 85.403(5) _cell_angle_gamma 62.334(4) _cell_volume 739.47(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3328 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 24.2 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 1.00 _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 'Bruker axs (Kappa apex2)' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6693 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2530 _reflns_number_gt 2033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (BRUKER, 2004)' _computing_cell_refinement 'APEX2/SAINT (BRUKER, 2004)' _computing_data_reduction 'SAINT/XPREP (BRUKER, 2004)' _computing_structure_solution 'SIR92 (WINGX)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP32 (WINGX)' _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^)+(0.0951P)^2^+1.5884P] 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 SHELXL _refine_ls_extinction_coef 0.111(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2530 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.2637 _refine_ls_wR_factor_gt 0.2441 _refine_ls_goodness_of_fit_ref 1.199 _refine_ls_restrained_S_all 1.199 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5363(7) 0.4688(7) 0.2759(3) 0.0423(11) Uani 1 1 d . . . H1 H 0.5339 0.3504 0.2500 0.051(14) Uiso 1 1 calc R . . C2 C 0.3202(8) 0.6083(8) 0.3173(3) 0.0480(12) Uani 1 1 d . . . H2 H 0.3129 0.7410 0.3295 0.070(17) Uiso 1 1 calc R . . C3 C 0.2639(9) 0.5286(10) 0.4010(4) 0.0657(16) Uani 1 1 d . . . H3A H 0.3636 0.5151 0.4417 0.065(16) Uiso 1 1 calc R . . H3B H 0.1278 0.6312 0.4244 0.11(3) Uiso 1 1 calc R . . C4 C 0.2578(11) 0.3265(13) 0.3961(5) 0.088(2) Uani 1 1 d . . . H4A H 0.1944 0.3091 0.4507 0.12(3) Uiso 1 1 calc R . . H4B H 0.1650 0.3380 0.3525 0.077(19) Uiso 1 1 calc R . . C5 C 0.4586(13) 0.1344(11) 0.3767(5) 0.082(2) Uani 1 1 d . . . H5A H 0.4899 0.1217 0.3148 0.08(2) Uiso 1 1 calc R . . H5B H 0.4359 0.0196 0.3947 0.053(14) Uiso 1 1 calc R . . C6 C 0.6489(11) 0.1156(11) 0.4172(5) 0.082(2) Uani 1 1 d . . . H6A H 0.7292 -0.0250 0.4339 0.075(18) Uiso 1 1 calc R . . H6B H 0.6019 0.1990 0.4695 0.12(3) Uiso 1 1 calc R . . C7 C 0.7940(11) 0.1755(11) 0.3629(5) 0.085(2) Uani 1 1 d . . . H7A H 0.9151 0.1413 0.3947 0.11(3) Uiso 1 1 calc R . . H7B H 0.8424 0.0895 0.3114 0.063(17) Uiso 1 1 calc R . . C8 C 0.7155(9) 0.3932(10) 0.3349(4) 0.0638(16) Uani 1 1 d . . . H8A H 0.8310 0.4068 0.3053 0.09(2) Uiso 1 1 calc R . . H8B H 0.6692 0.4812 0.3858 0.08(2) Uiso 1 1 calc R . . C9 C 0.6730(6) 0.4878(6) 0.1351(3) 0.0357(10) Uani 1 1 d . . . C10 C 0.7074(6) 0.6195(6) 0.0681(3) 0.0337(10) Uani 1 1 d . . . C11 C 0.7217(6) 0.7941(6) 0.0892(3) 0.0390(10) Uani 1 1 d . . . H11 H 0.7068 0.8345 0.1465 0.047 Uiso 1 1 calc R . . C12 C 0.7580(6) 0.9074(6) 0.0251(3) 0.0369(10) Uani 1 1 d . . . H12 H 0.7698 1.0234 0.0385 0.044 Uiso 1 1 calc R . . C13 C 0.7764(6) 0.8451(6) -0.0591(3) 0.0346(10) Uani 1 1 d . . . C14 C 0.7632(6) 0.6721(7) -0.0819(3) 0.0384(10) Uani 1 1 d . . . H14 H 0.7760 0.6333 -0.1393 0.046 Uiso 1 1 calc R . . C15 C 0.7309(6) 0.5601(7) -0.0174(3) 0.0379(10) Uani 1 1 d . . . H15 H 0.7245 0.4416 -0.0313 0.045 Uiso 1 1 calc R . . N1 N 0.8108(6) 0.9669(6) -0.1281(3) 0.0426(9) Uani 1 1 d . . . O1 O 0.1656(6) 0.6381(6) 0.2594(3) 0.0631(11) Uani 1 1 d . . . H1O H 0.1613 0.7220 0.2235 0.09(2) Uiso 1 1 calc R . . O2 O 0.5735(5) 0.5884(5) 0.2073(2) 0.0446(9) Uani 1 1 d . . . O3 O 0.7319(6) 0.3087(5) 0.1228(2) 0.0550(10) Uani 1 1 d . . . O4 O 0.8365(6) 1.1116(5) -0.1082(2) 0.0545(10) Uani 1 1 d . . . O5 O 0.8078(7) 0.9201(6) -0.2025(2) 0.0641(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.043(2) 0.041(3) 0.044(2) 0.0031(19) 0.0015(19) -0.022(2) C2 0.051(3) 0.049(3) 0.046(3) -0.002(2) 0.002(2) -0.025(2) C3 0.054(3) 0.082(4) 0.049(3) 0.006(3) 0.009(2) -0.023(3) C4 0.073(4) 0.123(6) 0.090(5) 0.049(4) -0.014(4) -0.065(5) C5 0.118(6) 0.076(4) 0.079(5) 0.020(3) -0.008(4) -0.066(5) C6 0.086(5) 0.069(4) 0.083(5) 0.035(4) -0.012(4) -0.029(4) C7 0.065(4) 0.085(5) 0.084(5) 0.036(4) -0.009(3) -0.018(3) C8 0.053(3) 0.079(4) 0.062(3) 0.021(3) -0.006(3) -0.034(3) C9 0.029(2) 0.032(2) 0.043(2) -0.0008(18) -0.0034(17) -0.0123(18) C10 0.0218(19) 0.030(2) 0.047(2) 0.0011(17) -0.0022(16) -0.0101(16) C11 0.034(2) 0.035(2) 0.043(2) -0.0033(18) -0.0045(17) -0.0115(19) C12 0.026(2) 0.029(2) 0.052(3) -0.0011(18) -0.0022(17) -0.0103(17) C13 0.0230(19) 0.029(2) 0.046(2) 0.0015(17) -0.0040(16) -0.0070(17) C14 0.034(2) 0.039(2) 0.040(2) -0.0025(18) -0.0030(17) -0.0152(19) C15 0.031(2) 0.034(2) 0.047(2) -0.0061(18) 0.0009(17) -0.0143(18) N1 0.034(2) 0.039(2) 0.051(2) 0.0035(17) -0.0029(16) -0.0139(17) O1 0.054(2) 0.067(3) 0.070(2) 0.022(2) -0.0139(18) -0.0297(19) O2 0.0516(19) 0.0351(17) 0.0433(17) 0.0000(13) 0.0068(14) -0.0185(15) O3 0.069(2) 0.0330(18) 0.059(2) -0.0038(15) 0.0091(17) -0.0219(17) O4 0.062(2) 0.0379(19) 0.069(2) 0.0096(16) -0.0073(17) -0.0276(17) O5 0.087(3) 0.067(2) 0.044(2) 0.0053(17) -0.0053(18) -0.041(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.464(5) . ? C1 C2 1.517(6) . ? C1 C8 1.532(7) . ? C1 H1 0.9800 . ? C2 O1 1.432(6) . ? C2 C3 1.526(7) . ? C2 H2 0.9800 . ? C3 C4 1.521(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.503(11) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.512(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.516(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.507(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O3 1.203(5) . ? C9 O2 1.321(5) . ? C9 C10 1.500(6) . ? C10 C15 1.385(6) . ? C10 C11 1.392(6) . ? C11 C12 1.380(6) . ? C11 H11 0.9300 . ? C12 C13 1.375(6) . ? C12 H12 0.9300 . ? C13 C14 1.382(6) . ? C13 N1 1.471(6) . ? C14 C15 1.366(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N1 O4 1.219(5) . ? N1 O5 1.222(5) . ? O1 H1O 0.8200 . ? 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 O2 C1 C2 105.1(4) . . ? O2 C1 C8 109.0(4) . . ? C2 C1 C8 116.3(4) . . ? O2 C1 H1 108.8 . . ? C2 C1 H1 108.8 . . ? C8 C1 H1 108.8 . . ? O1 C2 C1 110.1(4) . . ? O1 C2 C3 107.5(4) . . ? C1 C2 C3 114.0(4) . . ? O1 C2 H2 108.4 . . ? C1 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? C4 C3 C2 117.2(5) . . ? C4 C3 H3A 108.0 . . ? C2 C3 H3A 108.0 . . ? C4 C3 H3B 108.0 . . ? C2 C3 H3B 108.0 . . ? H3A C3 H3B 107.3 . . ? C5 C4 C3 119.0(5) . . ? C5 C4 H4A 107.6 . . ? C3 C4 H4A 107.6 . . ? C5 C4 H4B 107.6 . . ? C3 C4 H4B 107.6 . . ? H4A C4 H4B 107.0 . . ? C4 C5 C6 117.1(7) . . ? C4 C5 H5A 108.0 . . ? C6 C5 H5A 108.0 . . ? C4 C5 H5B 108.0 . . ? C6 C5 H5B 108.0 . . ? H5A C5 H5B 107.3 . . ? C5 C6 C7 117.0(6) . . ? C5 C6 H6A 108.1 . . ? C7 C6 H6A 108.1 . . ? C5 C6 H6B 108.1 . . ? C7 C6 H6B 108.1 . . ? H6A C6 H6B 107.3 . . ? C8 C7 C6 119.6(6) . . ? C8 C7 H7A 107.4 . . ? C6 C7 H7A 107.4 . . ? C8 C7 H7B 107.4 . . ? C6 C7 H7B 107.4 . . ? H7A C7 H7B 107.0 . . ? C7 C8 C1 115.1(5) . . ? C7 C8 H8A 108.5 . . ? C1 C8 H8A 108.5 . . ? C7 C8 H8B 108.5 . . ? C1 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? O3 C9 O2 124.5(4) . . ? O3 C9 C10 122.2(4) . . ? O2 C9 C10 113.3(4) . . ? C15 C10 C11 119.5(4) . . ? C15 C10 C9 118.1(4) . . ? C11 C10 C9 122.3(4) . . ? C12 C11 C10 120.0(4) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 118.5(4) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C14 122.7(4) . . ? C12 C13 N1 119.0(4) . . ? C14 C13 N1 118.2(4) . . ? C15 C14 C13 117.9(4) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? C14 C15 C10 121.3(4) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? O4 N1 O5 123.4(4) . . ? O4 N1 C13 118.4(4) . . ? O5 N1 C13 118.2(4) . . ? C2 O1 H1O 109.5 . . ? C9 O2 C1 116.2(3) . . ? 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 O2 C1 C2 O1 69.4(5) . . . . ? C8 C1 C2 O1 -170.0(4) . . . . ? O2 C1 C2 C3 -169.8(4) . . . . ? C8 C1 C2 C3 -49.2(6) . . . . ? O1 C2 C3 C4 60.9(6) . . . . ? C1 C2 C3 C4 -61.4(7) . . . . ? C2 C3 C4 C5 68.4(8) . . . . ? C3 C4 C5 C6 38.9(9) . . . . ? C4 C5 C6 C7 -96.0(8) . . . . ? C5 C6 C7 C8 63.6(10) . . . . ? C6 C7 C8 C1 -63.1(9) . . . . ? O2 C1 C8 C7 -138.0(5) . . . . ? C2 C1 C8 C7 103.6(6) . . . . ? O3 C9 C10 C15 25.3(6) . . . . ? O2 C9 C10 C15 -154.7(4) . . . . ? O3 C9 C10 C11 -153.0(4) . . . . ? O2 C9 C10 C11 27.0(5) . . . . ? C15 C10 C11 C12 0.3(6) . . . . ? C9 C10 C11 C12 178.6(4) . . . . ? C10 C11 C12 C13 0.9(6) . . . . ? C11 C12 C13 C14 -1.0(6) . . . . ? C11 C12 C13 N1 178.8(4) . . . . ? C12 C13 C14 C15 -0.1(6) . . . . ? N1 C13 C14 C15 -179.9(4) . . . . ? C13 C14 C15 C10 1.4(6) . . . . ? C11 C10 C15 C14 -1.5(6) . . . . ? C9 C10 C15 C14 -179.8(4) . . . . ? C12 C13 N1 O4 5.1(5) . . . . ? C14 C13 N1 O4 -175.1(4) . . . . ? C12 C13 N1 O5 -173.5(4) . . . . ? C14 C13 N1 O5 6.3(6) . . . . ? O3 C9 O2 C1 0.5(6) . . . . ? C10 C9 O2 C1 -179.5(3) . . . . ? C2 C1 O2 C9 -141.7(4) . . . . ? C8 C1 O2 C9 93.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.464 _refine_diff_density_min -0.517 _refine_diff_density_rms 0.171 #======================================================================= data_new _database_code_depnum_ccdc_archive 'CCDC 622916' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 N2 O3' _chemical_formula_sum 'C12 H16 N2 O3' _chemical_formula_weight 236.27 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.6930(18) _cell_length_b 9.9424(8) _cell_length_c 14.9984(16) _cell_angle_alpha 90.00 _cell_angle_beta 122.342(10) _cell_angle_gamma 90.00 _cell_volume 2355.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4732 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 31.0 _exptl_crystal_description prisamatic _exptl_crystal_colour brown _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9230 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker axs (Kappa Apex2)' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16478 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _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 2.42 _diffrn_reflns_theta_max 32.23 _reflns_number_total 4148 _reflns_number_gt 2723 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP32 (WINGX)' _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^)+(0.1000P)^2^+0.0194P] 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 4148 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1973 _refine_ls_wR_factor_gt 0.1701 _refine_ls_goodness_of_fit_ref 1.279 _refine_ls_restrained_S_all 1.279 _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 N1 N 0.02113(6) 0.66982(10) 0.42215(8) 0.0448(3) Uani 1 1 d . . . H1 H -0.0132 0.6116 0.4214 0.054 Uiso 1 1 calc R . . N2 N -0.09668(9) 1.19667(12) 0.31892(10) 0.0601(3) Uani 1 1 d . . . C1 C -0.06761(9) 1.06012(13) 0.34195(10) 0.0470(3) Uani 1 1 d . . . C2 C -0.12120(9) 0.95824(14) 0.33454(10) 0.0491(3) Uani 1 1 d . . . H2 H -0.1769 0.9776 0.3127 0.059 Uiso 1 1 calc R . . C3 C -0.09163(8) 0.82864(13) 0.35955(10) 0.0448(3) Uani 1 1 d . . . H3 H -0.1279 0.7602 0.3534 0.054 Uiso 1 1 calc R . . C4 C -0.00669(7) 0.79787(12) 0.39460(9) 0.0398(3) Uani 1 1 d . . . C5 C 0.04557(8) 0.90343(14) 0.39946(10) 0.0491(3) Uani 1 1 d . . . H5 H 0.1013 0.8853 0.4205 0.059 Uiso 1 1 calc R . . C6 C 0.01543(9) 1.03252(13) 0.37363(11) 0.0515(3) Uani 1 1 d . . . H6 H 0.0506 1.1014 0.3774 0.062 Uiso 1 1 calc R . . C7 C 0.10516(7) 0.62425(12) 0.45291(9) 0.0399(3) Uani 1 1 d . . . H7 H 0.1463 0.6918 0.5000 0.048 Uiso 1 1 calc R . . C8 C 0.12606(8) 0.49135(11) 0.51285(10) 0.0413(3) Uani 1 1 d . . . H8 H 0.0863 0.4235 0.4641 0.050 Uiso 1 1 calc R . . C9 C 0.21493(8) 0.44657(15) 0.54656(11) 0.0520(3) Uani 1 1 d . . . H9A H 0.2272 0.3612 0.5833 0.062 Uiso 1 1 calc R . . H9B H 0.2555 0.5121 0.5952 0.062 Uiso 1 1 calc R . . C10 C 0.22489(9) 0.43131(17) 0.45280(13) 0.0616(4) Uani 1 1 d . . . H10A H 0.2830 0.4075 0.4777 0.074 Uiso 1 1 calc R . . H10B H 0.1886 0.3593 0.4076 0.074 Uiso 1 1 calc R . . C11 C 0.20202(9) 0.56045(19) 0.39012(13) 0.0627(4) Uani 1 1 d . . . H11A H 0.2039 0.5462 0.3274 0.075 Uiso 1 1 calc R . . H11B H 0.2430 0.6296 0.4323 0.075 Uiso 1 1 calc R . . C12 C 0.11416(8) 0.60675(17) 0.35831(10) 0.0536(3) Uani 1 1 d . . . H12A H 0.0729 0.5414 0.3103 0.064 Uiso 1 1 calc R . . H12B H 0.1019 0.6917 0.3210 0.064 Uiso 1 1 calc R . . O1 O 0.11673(7) 0.49809(9) 0.60083(8) 0.0532(3) Uani 1 1 d . . . H1A H 0.1283 0.5742 0.6258 0.080 Uiso 1 1 calc R . . O2 O -0.16719(8) 1.22366(12) 0.30363(10) 0.0773(4) Uani 1 1 d . . . O3 O -0.05126(10) 1.28356(13) 0.31526(12) 0.0886(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0383(5) 0.0443(5) 0.0541(6) 0.0103(4) 0.0261(5) 0.0077(4) N2 0.0781(9) 0.0477(6) 0.0525(7) -0.0006(5) 0.0336(6) 0.0136(6) C1 0.0598(8) 0.0431(6) 0.0369(6) 0.0010(5) 0.0249(6) 0.0108(5) C2 0.0493(7) 0.0549(7) 0.0468(7) 0.0031(5) 0.0282(6) 0.0146(6) C3 0.0440(6) 0.0471(6) 0.0481(7) 0.0043(5) 0.0278(6) 0.0072(5) C4 0.0405(6) 0.0440(6) 0.0343(5) 0.0046(4) 0.0196(5) 0.0069(4) C5 0.0398(6) 0.0498(7) 0.0501(7) 0.0075(5) 0.0190(6) 0.0039(5) C6 0.0529(7) 0.0481(7) 0.0449(7) 0.0038(5) 0.0205(6) -0.0003(5) C7 0.0326(5) 0.0426(6) 0.0404(6) 0.0059(4) 0.0168(5) 0.0050(4) C8 0.0407(6) 0.0372(5) 0.0421(6) -0.0002(4) 0.0196(5) 0.0026(4) C9 0.0447(7) 0.0485(7) 0.0519(7) 0.0056(5) 0.0187(6) 0.0117(5) C10 0.0456(7) 0.0684(9) 0.0695(10) -0.0050(7) 0.0299(7) 0.0132(6) C11 0.0446(7) 0.0883(11) 0.0615(9) 0.0074(8) 0.0324(7) 0.0109(7) C12 0.0402(6) 0.0756(9) 0.0444(7) 0.0125(6) 0.0223(6) 0.0129(6) O1 0.0709(7) 0.0426(5) 0.0534(6) 0.0065(4) 0.0381(5) 0.0048(4) O2 0.0853(9) 0.0586(7) 0.0884(9) 0.0005(6) 0.0468(7) 0.0266(6) O3 0.1058(11) 0.0481(6) 0.1148(11) 0.0117(6) 0.0610(9) 0.0077(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 N1 C4 1.3536(15) . ? N1 C7 1.4525(14) . ? N1 H1 0.8600 . ? N2 O3 1.2330(19) . ? N2 O2 1.2403(17) . ? N2 C1 1.4342(17) . ? C1 C6 1.386(2) . ? C1 C2 1.387(2) . ? C2 C3 1.3729(17) . ? C2 H2 0.9300 . ? C3 C4 1.4135(16) . ? C3 H3 0.9300 . ? C4 C5 1.4088(18) . ? C5 C6 1.3716(18) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.5254(17) . ? C7 C8 1.5267(16) . ? C7 H7 0.9800 . ? C8 O1 1.4220(15) . ? C8 C9 1.5216(17) . ? C8 H8 0.9800 . ? C9 C10 1.522(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.512(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.5162(18) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? O1 H1A 0.8200 . ? 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 C4 N1 C7 124.33(10) . . ? C4 N1 H1 117.8 . . ? C7 N1 H1 117.8 . . ? O3 N2 O2 121.96(13) . . ? O3 N2 C1 119.52(14) . . ? O2 N2 C1 118.53(13) . . ? C6 C1 C2 120.75(12) . . ? C6 C1 N2 118.72(13) . . ? C2 C1 N2 120.52(13) . . ? C3 C2 C1 119.72(12) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.84(12) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? N1 C4 C5 122.85(11) . . ? N1 C4 C3 119.26(11) . . ? C5 C4 C3 117.89(11) . . ? C6 C5 C4 120.92(12) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 119.83(13) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N1 C7 C12 112.26(10) . . ? N1 C7 C8 110.46(10) . . ? C12 C7 C8 109.16(10) . . ? N1 C7 H7 108.3 . . ? C12 C7 H7 108.3 . . ? C8 C7 H7 108.3 . . ? O1 C8 C9 111.07(10) . . ? O1 C8 C7 112.70(9) . . ? C9 C8 C7 109.81(10) . . ? O1 C8 H8 107.7 . . ? C9 C8 H8 107.7 . . ? C7 C8 H8 107.7 . . ? C8 C9 C10 111.94(11) . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 110.88(12) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 110.60(13) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C7 112.45(11) . . ? C11 C12 H12A 109.1 . . ? C7 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C7 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C8 O1 H1A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 N2 C1 C6 8.69(19) . . . . ? O2 N2 C1 C6 -171.03(12) . . . . ? O3 N2 C1 C2 -172.52(14) . . . . ? O2 N2 C1 C2 7.76(18) . . . . ? C6 C1 C2 C3 0.47(19) . . . . ? N2 C1 C2 C3 -178.30(11) . . . . ? C1 C2 C3 C4 1.11(19) . . . . ? C7 N1 C4 C5 -4.22(19) . . . . ? C7 N1 C4 C3 175.96(10) . . . . ? C2 C3 C4 N1 177.67(11) . . . . ? C2 C3 C4 C5 -2.16(18) . . . . ? N1 C4 C5 C6 -178.13(12) . . . . ? C3 C4 C5 C6 1.69(19) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C2 C1 C6 C5 -0.9(2) . . . . ? N2 C1 C6 C5 177.85(12) . . . . ? C4 N1 C7 C12 -76.78(15) . . . . ? C4 N1 C7 C8 161.13(11) . . . . ? N1 C7 C8 O1 -54.38(13) . . . . ? C12 C7 C8 O1 -178.27(10) . . . . ? N1 C7 C8 C9 -178.77(10) . . . . ? C12 C7 C8 C9 57.34(13) . . . . ? O1 C8 C9 C10 176.89(11) . . . . ? C7 C8 C9 C10 -57.78(15) . . . . ? C8 C9 C10 C11 56.08(17) . . . . ? C9 C10 C11 C12 -54.14(19) . . . . ? C10 C11 C12 C7 56.24(19) . . . . ? N1 C7 C12 C11 179.46(12) . . . . ? C8 C7 C12 C11 -57.72(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 32.23 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.294 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.044