# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_(-)-(2R,3S)-2a _database_code_depnum_ccdc_archive 'CCDC 869566' #TrackingRef 'Org Lett 02-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; SAW694 IC-1 ; _chemical_melting_point ? _chemical_compound_source ? _chemical_absolute_configuration ad _chemical_formula_iupac ? _chemical_formula_moiety 'C12 H17 N1 O3' _chemical_formula_sum 'C12 H17 N1 O3' _chemical_formula_weight 223.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.5034(2) _cell_length_b 12.2919(4) _cell_length_c 13.0178(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1200.65(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 4898 _cell_measurement_theta_min 3.3922 _cell_measurement_theta_max 76.3036 _exptl_crystal_description lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.725 _exptl_absorpt_correction_T_min 0.57285 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_detector_area_resol_mean 10.5598 _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11172 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 9.02 _diffrn_reflns_theta_max 74.39 _reflns_number_total 2448 _reflns_number_gt 2287 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXTL (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2001)' _computing_molecular_graphics ; SHELXTL (Sheldrick, 2001), Mercury 2.4 (Macrae et al., 1998) ; _computing_publication_material ; SHELXTL (Sheldrick, 2001), Mercury 2.4 (Macrae et al., 1998) ; _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^)+(0.0415P)^2^+0.1550P] 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 mixed _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 -0.03(17) _refine_ls_number_reflns 2448 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.02983(13) 0.46448(8) 0.20018(7) 0.0208(2) Uani 1 1 d . . . H1A H -0.042(3) 0.4848(19) 0.1516(19) 0.046(6) Uiso 1 1 d . . . O2 O 0.18347(13) 0.58536(9) 0.04930(7) 0.0251(2) Uani 1 1 d . . . O3 O 0.36930(13) 0.66489(8) 0.16178(8) 0.0242(2) Uani 1 1 d . . . N1 N -0.26218(15) 0.52063(9) 0.54829(9) 0.0223(2) Uani 1 1 d . . . C1 C -0.00275(17) 0.61583(10) 0.48251(10) 0.0187(3) Uani 1 1 d . . . C2 C 0.16238(19) 0.67909(12) 0.51061(11) 0.0251(3) Uani 1 1 d . . . H2A H 0.1522 0.7536 0.4844 0.038 Uiso 1 1 calc R . . H2B H 0.2671 0.6440 0.4802 0.038 Uiso 1 1 calc R . . H2C H 0.1752 0.6808 0.5855 0.038 Uiso 1 1 calc R . . C3 C -0.11015(18) 0.57544(11) 0.56143(10) 0.0211(3) Uani 1 1 d . . . H3A H -0.0720 0.5880 0.6300 0.025 Uiso 1 1 calc R . . C4 C -0.31369(17) 0.50382(11) 0.45048(11) 0.0221(3) Uani 1 1 d . . . H4A H -0.4213 0.4651 0.4384 0.027 Uiso 1 1 calc R . . C5 C -0.21701(18) 0.54037(11) 0.36683(10) 0.0213(3) Uani 1 1 d . . . H5A H -0.2586 0.5260 0.2992 0.026 Uiso 1 1 calc R . . C6 C -0.05918(17) 0.59807(10) 0.38104(9) 0.0176(3) Uani 1 1 d . . . C7 C 0.04208(18) 0.64251(10) 0.28871(10) 0.0186(3) Uani 1 1 d . . . H7A H 0.1331 0.6950 0.3149 0.022 Uiso 1 1 calc R . . C8 C -0.08269(19) 0.70499(11) 0.21646(10) 0.0219(3) Uani 1 1 d . . . H8A H -0.1555 0.7558 0.2565 0.033 Uiso 1 1 calc R . . H8B H -0.1605 0.6535 0.1805 0.033 Uiso 1 1 calc R . . H8C H -0.0118 0.7456 0.1662 0.033 Uiso 1 1 calc R . . C9 C 0.14376(18) 0.54918(10) 0.23133(10) 0.0184(2) Uani 1 1 d . . . C10 C 0.28409(18) 0.49782(12) 0.30065(10) 0.0225(3) Uani 1 1 d . . . H10A H 0.3491 0.4418 0.2623 0.034 Uiso 1 1 calc R . . H10B H 0.2258 0.4647 0.3603 0.034 Uiso 1 1 calc R . . H10C H 0.3676 0.5539 0.3239 0.034 Uiso 1 1 calc R . . C11 C 0.23241(17) 0.59990(11) 0.13658(10) 0.0190(3) Uani 1 1 d . . . C12 C 0.4570(2) 0.71678(13) 0.07555(11) 0.0275(3) Uani 1 1 d . . . H12A H 0.5533 0.7636 0.1008 0.041 Uiso 1 1 calc R . . H12B H 0.3705 0.7609 0.0375 0.041 Uiso 1 1 calc R . . H12C H 0.5067 0.6610 0.0300 0.041 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 0.0259(5) 0.0172(4) 0.0194(4) -0.0003(3) -0.0013(4) -0.0020(4) O2 0.0285(5) 0.0311(5) 0.0156(4) -0.0005(4) -0.0002(4) -0.0021(4) O3 0.0252(5) 0.0278(5) 0.0195(4) 0.0039(4) 0.0002(4) -0.0065(4) N1 0.0226(5) 0.0223(5) 0.0219(5) 0.0038(5) 0.0024(4) 0.0012(5) C1 0.0223(6) 0.0158(6) 0.0180(6) 0.0005(4) -0.0011(5) 0.0004(5) C2 0.0289(7) 0.0282(7) 0.0183(6) -0.0013(5) -0.0038(5) -0.0071(6) C3 0.0253(6) 0.0211(6) 0.0170(6) 0.0019(5) -0.0009(5) 0.0016(5) C4 0.0204(6) 0.0216(6) 0.0243(6) 0.0010(5) -0.0003(5) -0.0013(5) C5 0.0217(6) 0.0226(6) 0.0197(6) -0.0020(5) -0.0017(5) -0.0006(5) C6 0.0198(6) 0.0160(6) 0.0170(6) -0.0005(5) 0.0005(5) 0.0021(5) C7 0.0212(6) 0.0179(6) 0.0168(6) 0.0000(5) -0.0009(5) -0.0012(5) C8 0.0287(7) 0.0184(6) 0.0186(6) 0.0011(5) -0.0006(5) 0.0049(5) C9 0.0202(6) 0.0193(6) 0.0157(5) 0.0016(5) 0.0003(5) -0.0003(5) C10 0.0224(6) 0.0262(7) 0.0188(6) 0.0022(5) -0.0012(5) 0.0032(5) C11 0.0192(6) 0.0190(6) 0.0186(6) 0.0004(5) 0.0002(5) 0.0020(5) C12 0.0281(7) 0.0288(7) 0.0255(7) 0.0076(5) 0.0050(6) -0.0038(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 O1 C9 1.4068(16) . y O1 H1A 0.87(2) . y O2 C11 1.2074(17) . y O3 C11 1.3419(16) . y O3 C12 1.4492(16) . y N1 C3 1.3359(19) . y N1 C4 1.3465(18) . y C1 C3 1.3969(19) . y C1 C6 1.4042(18) . y C1 C2 1.5079(18) . y C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9500 . ? C4 C5 1.3835(19) . y C4 H4A 0.9500 . ? C5 C6 1.3928(19) . y C5 H5A 0.9500 . ? C6 C7 1.5232(17) . y C7 C8 1.5332(17) . y C7 C9 1.5672(18) . y C7 H7A 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5237(18) . y C9 C11 1.5339(17) . y C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 C9 O1 H1A 111.9(16) . . y C11 O3 C12 114.86(11) . . y C3 N1 C4 116.33(11) . . y C3 C1 C6 117.56(12) . . y C3 C1 C2 118.61(12) . . y C6 C1 C2 123.79(12) . . y C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C1 125.29(13) . . y N1 C3 H3A 117.4 . . ? C1 C3 H3A 117.4 . . ? N1 C4 C5 122.96(12) . . y N1 C4 H4A 118.5 . . ? C5 C4 H4A 118.5 . . ? C4 C5 C6 120.44(12) . . y C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C1 117.42(12) . . y C5 C6 C7 120.13(11) . . y C1 C6 C7 122.42(12) . . y C6 C7 C8 111.05(11) . . y C6 C7 C9 110.88(10) . . y C8 C7 C9 111.81(10) . . y C6 C7 H7A 107.6 . . ? C8 C7 H7A 107.6 . . ? C9 C7 H7A 107.6 . . ? 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 . . ? O1 C9 C10 106.50(11) . . y O1 C9 C11 109.42(10) . . y C10 C9 C11 110.18(11) . . y O1 C9 C7 112.54(10) . . y C10 C9 C7 110.94(10) . . y C11 C9 C7 107.27(10) . . y C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 O3 123.44(12) . . y O2 C11 C9 124.38(12) . . y O3 C11 C9 112.17(11) . . y O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C3 C1 0.0(2) . . . . y C6 C1 C3 N1 0.4(2) . . . . y C2 C1 C3 N1 178.17(13) . . . . y C3 N1 C4 C5 0.02(19) . . . . y N1 C4 C5 C6 -0.4(2) . . . . y C4 C5 C6 C1 0.79(19) . . . . y C4 C5 C6 C7 -177.20(12) . . . . y C3 C1 C6 C5 -0.74(18) . . . . y C2 C1 C6 C5 -178.42(12) . . . . y C3 C1 C6 C7 177.20(12) . . . . y C2 C1 C6 C7 -0.48(19) . . . . y C5 C6 C7 C8 49.36(15) . . . . y C1 C6 C7 C8 -128.53(13) . . . . y C5 C6 C7 C9 -75.59(14) . . . . y C1 C6 C7 C9 106.52(14) . . . . y C6 C7 C9 O1 56.40(14) . . . . y C8 C7 C9 O1 -68.12(14) . . . . y C6 C7 C9 C10 -62.82(14) . . . . y C8 C7 C9 C10 172.66(11) . . . . y C6 C7 C9 C11 176.80(10) . . . . y C8 C7 C9 C11 52.28(14) . . . . y C12 O3 C11 O2 -0.47(19) . . . . y C12 O3 C11 C9 -179.05(11) . . . . y O1 C9 C11 O2 14.54(18) . . . . y C10 C9 C11 O2 131.31(14) . . . . y C7 C9 C11 O2 -107.82(14) . . . . y O1 C9 C11 O3 -166.90(10) . . . . y C10 C9 C11 O3 -50.12(14) . . . . y C7 C9 C11 O3 70.74(13) . . . . y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1A N1 0.87(2) 2.00(2) 2.8242(15) 160(2) 2_464 y _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 74.39 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.152 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.033 data_(+)-(2S,3S)-2b _database_code_depnum_ccdc_archive 'CCDC 869567' #TrackingRef 'Org Lett 02-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H17 N O3' _chemical_formula_sum 'C12 H17 N O3' _chemical_formula_weight 223.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.97836(4) _cell_length_b 12.67070(7) _cell_length_c 15.76352(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1194.087(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 38525 _cell_measurement_theta_min 2.8009 _cell_measurement_theta_max 72.3262 _exptl_crystal_description shards _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.729 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.839 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) 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 173 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44547 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0076 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.48 _diffrn_reflns_theta_max 72.48 _reflns_number_total 2366 _reflns_number_gt 2337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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. Results of chirality/polarity tests _refine_ls_R_factor_obs+ 0.0262 _refine_ls_wR_factor_obs+ 0.0723 _refine_ls_abs_structure_Flack+ 0.00(16) _refine_ls_R_factor_obs- 0.0264 _refine_ls_wR_factor_obs- 0.0729 _refine_ls_abs_structure_Flack- 1.05(16) ; _chemical_absolute_configuration ad _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^)+(0.0444P)^2^+0.1449P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0157(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 967 Friedel pairs' _refine_ls_abs_structure_Flack -0.05(16) _refine_ls_number_reflns 2366 _refine_ls_number_parameters 152 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0726 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.2477(2) 0.47905(8) 0.88035(6) 0.0379(2) Uani 1 1 d . . . C2 C 0.4275(2) 0.54026(9) 0.88713(7) 0.0357(3) Uani 1 1 d . . . H2A H 0.4875 0.5505 0.9423 0.043 Uiso 1 1 calc R . . C3 C 0.53481(19) 0.59040(8) 0.82019(6) 0.0305(2) Uani 1 1 d . . . C4 C 0.44423(19) 0.57645(8) 0.73849(6) 0.0270(2) Uani 1 1 d . . . C5 C 0.2538(2) 0.51402(9) 0.73099(7) 0.0320(2) Uani 1 1 d . . . H5A H 0.1861 0.5039 0.6771 0.038 Uiso 1 1 calc R . . C6 C 0.1629(2) 0.46664(10) 0.80248(7) 0.0366(3) Uani 1 1 d . . . H6A H 0.0344 0.4233 0.7958 0.044 Uiso 1 1 calc R . . C7 C 0.7350(2) 0.65823(10) 0.83850(8) 0.0404(3) Uani 1 1 d . . . H7A H 0.7909 0.6427 0.8956 0.061 Uiso 1 1 calc R . . H7B H 0.6923 0.7328 0.8351 0.061 Uiso 1 1 calc R . . H7C H 0.8525 0.6435 0.7968 0.061 Uiso 1 1 calc R . . C8 C 0.54528(19) 0.63412(8) 0.66347(6) 0.0291(2) Uani 1 1 d . . . H8A H 0.7094 0.6408 0.6745 0.035 Uiso 1 1 calc R . . C9 C 0.51755(17) 0.57986(9) 0.57600(6) 0.0273(2) Uani 1 1 d . . . C10 C 0.56549(19) 0.46082(8) 0.58074(6) 0.0287(2) Uani 1 1 d . . . O10 O 0.44277(16) 0.39269(6) 0.55593(6) 0.0425(2) Uani 1 1 d . . . O11 O 0.76992(15) 0.44240(6) 0.61221(6) 0.0416(2) Uani 1 1 d . . . C12 C 0.8440(3) 0.33381(10) 0.61121(10) 0.0507(3) Uani 1 1 d . . . H12A H 0.7997 0.3008 0.5576 0.076 Uiso 1 1 calc R . . H12B H 0.7753 0.2956 0.6586 0.076 Uiso 1 1 calc R . . H12C H 1.0072 0.3314 0.6168 0.076 Uiso 1 1 calc R . . C13 C 0.4480(3) 0.74640(9) 0.66133(7) 0.0414(3) Uani 1 1 d . . . H13A H 0.4675 0.7797 0.7170 0.062 Uiso 1 1 calc R . . H13B H 0.2883 0.7431 0.6475 0.062 Uiso 1 1 calc R . . H13C H 0.5261 0.7881 0.6181 0.062 Uiso 1 1 calc R . . O14 O 0.29596(13) 0.59515(6) 0.54764(5) 0.03130(19) Uani 1 1 d D . . H14 H 0.289(3) 0.5731(14) 0.4934(4) 0.062(5) Uiso 1 1 d D . . C15 C 0.6838(2) 0.62686(9) 0.51219(7) 0.0359(3) Uani 1 1 d . . . H15A H 0.6652 0.5921 0.4571 0.054 Uiso 1 1 calc R . . H15B H 0.8368 0.6158 0.5326 0.054 Uiso 1 1 calc R . . H15C H 0.6556 0.7027 0.5061 0.054 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 N1 0.0484(6) 0.0400(5) 0.0254(4) 0.0037(4) 0.0066(4) 0.0029(5) C2 0.0487(7) 0.0363(5) 0.0221(5) -0.0004(4) -0.0024(5) 0.0068(5) C3 0.0371(6) 0.0291(5) 0.0253(5) -0.0013(4) -0.0044(4) 0.0039(4) C4 0.0318(5) 0.0269(5) 0.0224(4) 0.0003(4) -0.0014(4) 0.0030(4) C5 0.0340(6) 0.0375(5) 0.0244(5) 0.0004(4) 0.0002(4) -0.0021(5) C6 0.0378(6) 0.0421(6) 0.0299(5) 0.0021(5) 0.0043(5) -0.0040(5) C7 0.0450(6) 0.0431(6) 0.0331(6) -0.0048(5) -0.0117(5) -0.0024(5) C8 0.0325(5) 0.0314(5) 0.0235(5) 0.0015(4) -0.0025(4) -0.0049(4) C9 0.0288(5) 0.0299(5) 0.0232(5) 0.0020(4) 0.0001(4) -0.0012(4) C10 0.0303(5) 0.0324(5) 0.0234(4) 0.0024(4) 0.0018(4) -0.0012(5) O10 0.0458(5) 0.0331(4) 0.0486(5) -0.0023(4) -0.0080(4) -0.0048(4) O11 0.0353(4) 0.0343(4) 0.0553(5) 0.0017(4) -0.0089(4) 0.0041(3) C12 0.0492(7) 0.0380(6) 0.0650(9) 0.0066(6) -0.0026(7) 0.0118(6) C13 0.0675(8) 0.0289(5) 0.0280(5) 0.0001(4) -0.0011(6) -0.0014(6) O14 0.0313(4) 0.0397(4) 0.0230(3) -0.0024(3) -0.0037(3) 0.0039(3) C15 0.0403(6) 0.0370(6) 0.0303(5) 0.0051(4) 0.0072(5) -0.0025(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 N1 C2 1.3299(18) . ? N1 C6 1.3372(16) . ? C2 C3 1.3888(16) . ? C3 C4 1.4083(14) . ? C3 C7 1.5014(17) . ? C4 C5 1.3915(16) . ? C4 C8 1.5158(14) . ? C5 C6 1.3877(15) . ? C8 C13 1.5373(16) . ? C8 C9 1.5496(14) . ? C9 O14 1.4115(12) . ? C9 C15 1.5345(15) . ? C9 C10 1.5371(15) . ? C10 O10 1.1985(14) . ? C10 O11 1.3395(14) . ? O11 C12 1.4454(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 116.67(10) . . ? N1 C2 C3 125.38(10) . . ? C2 C3 C4 117.38(10) . . ? C2 C3 C7 118.95(10) . . ? C4 C3 C7 123.65(10) . . ? C5 C4 C3 117.63(9) . . ? C5 C4 C8 122.27(9) . . ? C3 C4 C8 119.98(10) . . ? C6 C5 C4 119.82(10) . . ? N1 C6 C5 123.10(11) . . ? C4 C8 C13 108.21(9) . . ? C4 C8 C9 115.95(8) . . ? C13 C8 C9 110.53(9) . . ? O14 C9 C15 110.30(8) . . ? O14 C9 C10 108.97(9) . . ? C15 C9 C10 106.97(9) . . ? O14 C9 C8 108.75(8) . . ? C15 C9 C8 109.99(9) . . ? C10 C9 C8 111.85(8) . . ? O10 C10 O11 123.63(10) . . ? O10 C10 C9 125.23(10) . . ? O11 C10 C9 111.04(9) . . ? C10 O11 C12 116.19(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 72.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.161 _refine_diff_density_min -0.104 _refine_diff_density_rms 0.028 #===END