# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Frederic Minassian' _publ_contact_author_email FREDERIC.MINASSIAN@UJF-GRENOBLE.FR _publ_section_title ; Efficient Stereoselective Nucleophilic Addition of Pyrroles to Chiral Nitrones ; loop_ _publ_author_name 'Frederic Minassian' 'Christophe Berini' 'Jean-Noel Denis' 'Nadia Pelloux-Leon' 'Christian Philouze' ; Y.Vallee ; # Attachment 'file7a.cif.txt' data_Christophe _database_code_depnum_ccdc_archive 'CCDC 679400' #------------------------------------------------------------------------------ _audit_creation_date 2007-09-26 _audit_creation_method 'by teXsan v1.8' #------------------------------------------------------------------------------ _computing_data_collection 'Bruker-Enraf-Nonius kappaCCD' _computing_cell_refinement 'Bruker-Enraf-Nonius kappaCCD' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 11.778(2) _cell_length_b 16.333(3) _cell_length_c 21.185(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4075(1) _cell_formula_units_Z 8 _cell_measurement_temperature 150.0 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' '1/2-x, -y,1/2+z' ' -x, -y, -z' '1/2-x,1/2+y, +z' ' +x,1/2-y,1/2+z' '1/2+x, +y,1/2-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 389.51 _chemical_formula_analytical ? _chemical_formula_sum 'C20 H27 N3 O3 S ' _chemical_formula_moiety 'C20 H27 N3 O3 S ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1664.00 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 150.0 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector CCD _diffrn_measurement_device_type 'Bruker-Enraf-Nonius kappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? _diffrn_reflns_number 42538 _reflns_number_total 6520 _reflns_number_gt 3350 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.14478 _diffrn_reflns_av_sigmaI/netI 0.100 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 160 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N 0 24 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 24 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; S 0 8 0.110 0.124 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 216 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom S(1) 0.22428(5) 0.33282(3) 0.12263(3) 0.0326(1) 1.000 . Uani d ? O(8) -0.0058(1) 0.08562(8) 0.05319(6) 0.0190(3) 1.000 . Uani d ? O(11) 0.3180(1) 0.31328(9) -0.08101(7) 0.0240(3) 1.000 . Uani d ? O(12) 0.1545(1) 0.24012(9) -0.08757(6) 0.0234(3) 1.000 . Uani d ? N(1') 0.1821(1) 0.0524(1) -0.02568(8) 0.0189(4) 1.000 . Uani d ? N(3) 0.2194(1) 0.2778(1) 0.00643(7) 0.0185(4) 1.000 . Uani d ? N(7) 0.0769(1) 0.1133(1) 0.09967(7) 0.0152(3) 1.000 . Uani d ? C(1") 0.0433(2) 0.0303(1) 0.19540(9) 0.0171(4) 1.000 . Uani d ? C(2) 0.2933(2) 0.3265(1) 0.0465(1) 0.0287(5) 1.000 . Uani d ? C(2") -0.0564(2) 0.0725(1) 0.2066(1) 0.0256(5) 1.000 . Uani d ? C(2') 0.2337(2) 0.0990(1) 0.01936(8) 0.0166(4) 1.000 . Uani d ? C(3") -0.1147(2) 0.0617(2) 0.2629(1) 0.0342(6) 1.000 . Uani d ? C(3') 0.3488(2) 0.0878(1) 0.0130(1) 0.0236(5) 1.000 . Uani d ? C(4) 0.1285(2) 0.2343(1) 0.03901(9) 0.0170(4) 1.000 . Uani d ? C(4") -0.0739(2) 0.0087(1) 0.3086(1) 0.0301(5) 1.000 . Uani d ? C(4') 0.3659(2) 0.0325(1) -0.0376(1) 0.0275(5) 1.000 . Uani d ? C(5") 0.0252(2) -0.0335(1) 0.2977(1) 0.0260(5) 1.000 . Uani d ? C(5) 0.0924(2) 0.2926(1) 0.0914(1) 0.0250(5) 1.000 . Uani d ? C(5') 0.2619(2) 0.0115(1) -0.0603(1) 0.0236(5) 1.000 . Uani d ? C(6) 0.1713(1) 0.1519(1) 0.06590(8) 0.0148(4) 1.000 . Uani d ? C(6") 0.0837(2) -0.0227(1) 0.2415(1) 0.0220(5) 1.000 . Uani d ? C(9) 0.1113(2) 0.0412(1) 0.13566(9) 0.0209(5) 1.000 . Uani d ? C(10) 0.2366(2) 0.2792(1) -0.05648(9) 0.0180(4) 1.000 . Uani d ? C(13) 0.1541(2) 0.2372(1) -0.15739(9) 0.0247(5) 1.000 . Uani d ? C(14) 0.1446(2) 0.3223(2) -0.1839(1) 0.0377(6) 1.000 . Uani d ? C(15) 0.2580(3) 0.1927(2) -0.1806(1) 0.0491(7) 1.000 . Uani d ? C(16) 0.0474(3) 0.1891(2) -0.1707(1) 0.0584(8) 1.000 . Uani d ? H(1) -0.0728 0.1192 0.0552 0.024 1.000 . Uiso c ? H(2) 0.1024 0.0488 -0.0320 0.023 1.000 . Uiso c ? H(3) 0.3653 0.3007 0.0506 0.034 1.000 . Uiso c ? H(4) 0.3030 0.3797 0.0292 0.034 1.000 . Uiso c ? H(5) 0.0669 0.2250 0.0110 0.020 1.000 . Uiso c ? H(6) 0.0466 0.3355 0.0750 0.030 1.000 . Uiso c ? H(7) 0.0516 0.2641 0.1233 0.030 1.000 . Uiso c ? H(8) 0.2255 0.1658 0.0974 0.018 1.000 . Uiso c ? H(9) 0.1892 0.0466 0.1466 0.025 1.000 . Uiso c ? H(10) 0.1015 -0.0059 0.1100 0.025 1.000 . Uiso c ? H(11) 0.1436 0.3197 -0.2287 0.045 1.000 . Uiso c ? H(12) 0.2078 0.3539 -0.1705 0.045 1.000 . Uiso c ? H(13) 0.0765 0.3470 -0.1693 0.045 1.000 . Uiso c ? H(14) 0.3242 0.2207 -0.1667 0.059 1.000 . Uiso c ? H(15) 0.2572 0.1908 -0.2254 0.059 1.000 . Uiso c ? H(16) 0.2583 0.1385 -0.1643 0.059 1.000 . Uiso c ? H(17) 0.0377 0.1836 -0.2150 0.070 1.000 . Uiso c ? H(18) -0.0161 0.2170 -0.1533 0.070 1.000 . Uiso c ? H(19) 0.0534 0.1363 -0.1521 0.070 1.000 . Uiso c ? H(20) 0.4063 0.1126 0.0379 0.028 1.000 . Uiso c ? H(21) 0.4370 0.0135 -0.0530 0.033 1.000 . Uiso c ? H(22) 0.2473 -0.0251 -0.0942 0.028 1.000 . Uiso c ? H(23) -0.0852 0.1090 0.1756 0.031 1.000 . Uiso c ? H(24) -0.1832 0.0909 0.2702 0.041 1.000 . Uiso c ? H(25) -0.1139 0.0015 0.3471 0.036 1.000 . Uiso c ? H(26) 0.0536 -0.0702 0.3287 0.031 1.000 . Uiso c ? H(27) 0.1522 -0.0520 0.2344 0.026 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0438(3) 0.0308(3) 0.0232(2) -0.0118(3) 0.0077(2) -0.0126(2) O(8) 0.0124(5) 0.0232(6) 0.0213(7) -0.0007(5) -0.0019(5) 0.0005(6) O(11) 0.0217(6) 0.0288(7) 0.0217(7) -0.0095(6) 0.0030(6) 0.0005(6) O(12) 0.0272(7) 0.0271(7) 0.0160(7) -0.0130(6) 0.0020(6) -0.0015(6) N(1') 0.0171(7) 0.0198(7) 0.0197(8) -0.0021(7) 0.0025(6) -0.0022(7) N(3) 0.0204(7) 0.0183(7) 0.0166(7) -0.0071(7) 0.0022(6) -0.0017(6) N(7) 0.0133(6) 0.0184(7) 0.0138(7) 0.0008(6) -0.0006(6) 0.0016(6) C(1") 0.0170(8) 0.0174(8) 0.0168(9) -0.0036(8) -0.0022(7) 0.0015(7) C(2) 0.031(1) 0.036(1) 0.0188(9) -0.016(1) 0.0024(8) -0.0031(9) C(2") 0.0179(9) 0.037(1) 0.022(1) 0.0032(9) 0.0029(8) 0.0119(9) C(2') 0.0168(8) 0.0177(8) 0.0152(8) 0.0000(8) 0.0005(7) 0.0014(7) C(3") 0.0201(9) 0.052(1) 0.031(1) 0.008(1) 0.0078(9) 0.015(1) C(3') 0.0168(8) 0.030(1) 0.024(1) 0.0018(8) 0.0007(8) -0.0023(8) C(4) 0.0157(8) 0.0169(8) 0.0184(9) -0.0018(7) 0.0026(7) 0.0005(7) C(4") 0.024(1) 0.042(1) 0.024(1) -0.006(1) 0.0029(9) 0.0120(9) C(4') 0.0226(9) 0.031(1) 0.029(1) 0.0099(9) 0.0098(9) -0.0001(9) C(5") 0.031(1) 0.024(1) 0.023(1) -0.0037(9) -0.0022(9) 0.0094(8) C(5) 0.027(1) 0.0205(9) 0.027(1) 0.0026(9) 0.0096(9) -0.0021(8) C(5') 0.032(1) 0.0173(9) 0.0220(9) 0.0037(9) 0.0080(9) -0.0033(8) C(6) 0.0123(7) 0.0185(9) 0.0137(8) -0.0008(7) 0.0003(7) -0.0007(7) C(6") 0.0228(9) 0.0196(9) 0.024(1) 0.0008(8) -0.0006(8) 0.0033(8) C(9) 0.0194(8) 0.023(1) 0.0198(9) 0.0051(8) 0.0039(8) 0.0052(8) C(10) 0.0202(9) 0.0146(8) 0.0193(9) -0.0022(8) 0.0013(8) -0.0009(7) C(13) 0.033(1) 0.026(1) 0.0152(9) -0.0093(9) -0.0009(8) -0.0007(8) C(14) 0.038(1) 0.038(1) 0.038(1) -0.002(1) -0.009(1) 0.014(1) C(15) 0.073(2) 0.045(1) 0.029(1) 0.021(1) 0.006(1) -0.010(1) C(16) 0.075(2) 0.073(2) 0.027(1) -0.049(1) -0.007(1) -0.001(1) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00123|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3350 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_all 0.0603 _refine_ls_wR_factor_ref 0.0603 _refine_ls_goodness_of_fit_all 1.032 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_shift/su_max 0.0092 _refine_ls_shift/su_mean 0.0010 _refine_diff_density_min -0.34 _refine_diff_density_max 0.42 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.809(2) . . yes S1 C5 1.811(2) . . yes O8 N7 1.457(2) . . yes O8 H1 0.96 . . no O11 C10 1.225(2) . . yes O11 H1 1.78 . 2 no O12 C10 1.333(2) . . yes O12 C13 1.480(2) . . yes N1' C2' 1.363(2) . . yes N1' C5' 1.366(2) . . yes N1' H2 0.95 . . no N3 C2 1.452(2) . . yes N3 C4 1.459(2) . . yes N3 C10 1.348(2) . . yes N7 C6 1.464(2) . . yes N7 C9 1.460(2) . . yes C1" C2" 1.382(3) . . yes C1" C6" 1.389(3) . . yes C1" C9 1.509(3) . . yes C2 H3 0.95 . . no C2 H4 0.95 . . no C2" C3" 1.388(3) . . yes C2" H23 0.95 . . no C2' C3' 1.375(3) . . yes C2' C6 1.503(2) . . yes C3" C4" 1.385(3) . . yes C3" H24 0.95 . . no C3' C4' 1.416(3) . . yes C3' H20 0.95 . . no C4 C5 1.524(3) . . yes C4 C6 1.546(3) . . yes C4 H5 0.95 . . no C4" C5" 1.375(3) . . yes C4" H25 0.95 . . no C4' C5' 1.360(3) . . yes C4' H21 0.95 . . no C5" C6" 1.386(3) . . yes C5" H26 0.95 . . no C5 H6 0.95 . . no C5 H7 0.95 . . no C5' H22 0.95 . . no C6 H8 0.95 . . no C6" H27 0.95 . . no C9 H9 0.95 . . no C9 H10 0.95 . . no C13 C14 1.504(3) . . yes C13 C15 1.507(3) . . yes C13 C16 1.508(3) . . yes C14 H11 0.95 . . no C14 H12 0.95 . . no C14 H13 0.95 . . no C15 H14 0.95 . . no C15 H15 0.95 . . no C15 H16 0.95 . . no C16 H17 0.95 . . no C16 H18 0.95 . . no C16 H19 0.95 . . no H3 H4 1.55 . . no H6 H7 1.55 . . no H9 H10 1.55 . . no H11 H12 1.55 . . no H11 H13 1.55 . . no H12 H13 1.55 . . no H14 H15 1.55 . . no H14 H16 1.55 . . no H15 H16 1.55 . . no H17 H18 1.55 . . no H17 H19 1.55 . . no H18 H19 1.55 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C5 92.3(1) . . . yes N7 O8 H1 110.0 . . . no C10 O11 H1 135.8 . . 2 no C10 O12 C13 120.8(1) . . . yes C2' N1' C5' 110.0(2) . . . yes C2' N1' H2 125.0 . . . no C5' N1' H2 125.0 . . . no C2 N3 C4 115.5(2) . . . yes C2 N3 C10 118.6(2) . . . yes C4 N3 C10 125.8(2) . . . yes O8 N7 C6 108.1(1) . . . yes O8 N7 C9 106.8(1) . . . yes C6 N7 C9 113.0(1) . . . yes C2" C1" C6" 118.7(2) . . . yes C2" C1" C9 122.5(2) . . . yes C6" C1" C9 118.8(2) . . . yes S1 C2 N3 106.4(1) . . . yes S1 C2 H3 110.2 . . . no S1 C2 H4 110.2 . . . no N3 C2 H3 110.2 . . . no N3 C2 H4 110.2 . . . no H3 C2 H4 109.5 . . . no C1" C2" C3" 120.3(2) . . . yes C1" C2" H23 119.8 . . . no C3" C2" H23 119.8 . . . no N1' C2' C3' 107.2(2) . . . yes N1' C2' C6 124.2(2) . . . yes C3' C2' C6 128.6(2) . . . yes C2" C3" C4" 120.6(2) . . . yes C2" C3" H24 119.7 . . . no C4" C3" H24 119.7 . . . no C2' C3' C4' 107.5(2) . . . yes C2' C3' H20 126.3 . . . no C4' C3' H20 126.3 . . . no N3 C4 C5 104.1(2) . . . yes N3 C4 C6 111.1(1) . . . yes N3 C4 H5 110.0 . . . no C5 C4 C6 111.5(2) . . . yes C5 C4 H5 110.0 . . . no C6 C4 H5 110.0 . . . no C3" C4" C5" 119.3(2) . . . yes C3" C4" H25 120.3 . . . no C5" C4" H25 120.3 . . . no C3' C4' C5' 107.4(2) . . . yes C3' C4' H21 126.3 . . . no C5' C4' H21 126.3 . . . no C4" C5" C6" 120.2(2) . . . yes C4" C5" H26 119.9 . . . no C6" C5" H26 119.9 . . . no S1 C5 C4 104.7(1) . . . yes S1 C5 H6 110.7 . . . no S1 C5 H7 110.7 . . . no C4 C5 H6 110.7 . . . no C4 C5 H7 110.7 . . . no H6 C5 H7 109.5 . . . no N1' C5' C4' 107.9(2) . . . yes N1' C5' H22 126.0 . . . no C4' C5' H22 126.0 . . . no N7 C6 C2' 116.4(2) . . . yes N7 C6 C4 107.9(1) . . . yes N7 C6 H8 105.6 . . . no C2' C6 C4 114.7(1) . . . yes C2' C6 H8 105.6 . . . no C4 C6 H8 105.6 . . . no C1" C6" C5" 120.8(2) . . . yes C1" C6" H27 119.6 . . . no C5" C6" H27 119.6 . . . no N7 C9 C1" 112.7(2) . . . yes N7 C9 H9 108.7 . . . no N7 C9 H10 108.7 . . . no C1" C9 H9 108.7 . . . no C1" C9 H10 108.7 . . . no H9 C9 H10 109.5 . . . no O11 C10 O12 125.2(2) . . . yes O11 C10 N3 123.0(2) . . . yes O12 C10 N3 111.8(2) . . . yes O12 C13 C14 110.1(2) . . . yes O12 C13 C15 109.8(2) . . . yes O12 C13 C16 101.9(2) . . . yes C14 C13 C15 112.6(2) . . . yes C14 C13 C16 110.5(2) . . . yes C15 C13 C16 111.4(2) . . . yes C13 C14 H11 109.5 . . . no C13 C14 H12 109.5 . . . no C13 C14 H13 109.5 . . . no H11 C14 H12 109.5 . . . no H11 C14 H13 109.5 . . . no H12 C14 H13 109.5 . . . no C13 C15 H14 109.5 . . . no C13 C15 H15 109.5 . . . no C13 C15 H16 109.5 . . . no H14 C15 H15 109.5 . . . no H14 C15 H16 109.5 . . . no H15 C15 H16 109.5 . . . no C13 C16 H17 109.5 . . . no C13 C16 H18 109.5 . . . no C13 C16 H19 109.5 . . . no H17 C16 H18 109.5 . . . no H17 C16 H19 109.5 . . . no H18 C16 H19 109.5 . . . no O8 H1 O11 163.6 . . 2_455 no H12 H11 H13 60.0 . . . no H11 H12 H13 60.0 . . . no H11 H13 H12 60.0 . . . no H15 H14 H16 60.0 . . . no H14 H15 H16 60.0 . . . no H14 H16 H15 60.0 . . . no H18 H17 H19 60.0 . . . no H17 H18 H19 60.0 . . . no H17 H19 H18 60.0 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O8 O11 2.717(2) . 2_455 no O8 N1' 3.120(2) . 5 no O8 C5' 3.412(2) . 5 no O8 C2 3.482(2) . 2_455 no O8 O8 3.594(3) . 5 no O11 N7 3.301(2) . 2 no O11 C5' 3.400(2) . 6 no O11 C2" 3.570(2) . 2 no C6" C16 3.466(3) . 5 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A O8 H1 O11 0.96 1.78 2.717(2) 163.6 2_455 N1' H2 O8 0.95 2.29 2.825(2) 114.9 . # Attachment 'file7b.cif.txt' data_LEDSS _database_code_depnum_ccdc_archive 'CCDC 679401' #------------------------------------------------------------------------------ _computing_data_collection 'Bruker-Enraf-Nonius CAD4' _computing_cell_refinement 'Bruker-Enraf-Nonius CAD4' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 9.198(2) _cell_length_b 9.198(2) _cell_length_c 40.598(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3435(1) _cell_formula_units_Z 8 _cell_measurement_temperature 293.0 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43 21 2 ' _symmetry_Int_Tables_number 96 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y,1/2+z' 1/2-y,1/2+x,3/4+z 1/2+y,1/2-x,1/4+z ' +y, +x, -z' ' -y, -x,1/2-z' 1/2-x,1/2+y,3/4-z 1/2+x,1/2-y,1/4-z #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 302.37 _chemical_formula_analytical ? _chemical_formula_sum 'C17 H22 N2 O3 ' _chemical_formula_moiety 'C17 H22 N2 O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1296.00 _exptl_absorpt_coefficient_mu 0.653 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.0 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type CAD-4 _diffrn_measurement_method 'omega scans' _diffrn_standards_number 2 _diffrn_standards_interval_count 7200 _diffrn_standards_decay_% 5.84 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 2 16 2 -2 16 _diffrn_reflns_number 14003 _reflns_number_total 3668 _reflns_number_gt 2438 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.06361 _diffrn_reflns_av_sigmaI/netI 0.070 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 74.90 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.04983 _diffrn_orient_matrix_UB_12 -0.08959 _diffrn_orient_matrix_UB_13 0.00821 _diffrn_orient_matrix_UB_21 -0.03059 _diffrn_orient_matrix_UB_22 -0.02404 _diffrn_orient_matrix_UB_23 -0.02300 _diffrn_orient_matrix_UB_31 0.09165 _diffrn_orient_matrix_UB_32 -0.05669 _diffrn_orient_matrix_UB_33 -0.00321 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 136 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 176 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 16 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 24 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) -1.0008(2) -0.2269(2) -0.90401(4) 0.0857(5) 1.000 . Uani d ? O(3) -0.9460(2) -0.0026(1) -0.92307(3) 0.0582(4) 1.000 . Uani d ? O(10) -0.5850(1) 0.0074(1) -0.86043(3) 0.0555(4) 1.000 . Uani d ? N(1') -0.8076(2) 0.3525(2) -0.90016(5) 0.0600(5) 1.000 . Uani d ? N(9) -0.7286(2) 0.0545(2) -0.84883(4) 0.0461(5) 1.000 . Uani d ? C(1") -0.6529(2) 0.1317(2) -0.79351(5) 0.0497(6) 1.000 . Uani d ? C(2') -0.7448(2) 0.2181(2) -0.89892(5) 0.0445(5) 1.000 . Uani d ? C(2) -1.0187(2) -0.1330(2) -0.93155(6) 0.0619(7) 1.000 . Uani d ? C(2") -0.7346(3) 0.0352(3) -0.77540(6) 0.0762(8) 1.000 . Uani d ? C(3') -0.6254(2) 0.2243(2) -0.91871(5) 0.0580(7) 1.000 . Uani d ? C(3") -0.6961(3) -0.0064(3) -0.74448(6) 0.0857(9) 1.000 . Uani d ? C(4') -0.6181(3) 0.3635(3) -0.93291(7) 0.0769(8) 1.000 . Uani d ? C(4) -0.8396(2) -0.0372(2) -0.89887(5) 0.0506(6) 1.000 . Uani d ? C(4") -0.5701(3) 0.0453(3) -0.73081(6) 0.0849(9) 1.000 . Uani d ? C(5) -0.9120(3) -0.1591(2) -0.88007(5) 0.0668(7) 1.000 . Uani d ? C(5') -0.7318(3) 0.4401(3) -0.92087(7) 0.0774(8) 1.000 . Uani d ? C(5") -0.4849(3) 0.1393(3) -0.74849(6) 0.0848(9) 1.000 . Uani d ? C(6) -1.1758(3) -0.0988(3) -0.93599(8) 0.095(1) 1.000 . Uani d ? C(6") -0.5249(3) 0.1816(3) -0.77989(5) 0.0669(7) 1.000 . Uani d ? C(7) -0.9503(4) -0.2020(3) -0.96095(6) 0.097(1) 1.000 . Uani d ? C(8) -0.8096(2) 0.0983(2) -0.87860(5) 0.0431(5) 1.000 . Uani d ? C(11) -0.7021(2) 0.1786(2) -0.82696(5) 0.0514(6) 1.000 . Uani d ? H(12) -0.5722 -0.1005 -0.8516 0.112 1.000 . Uiso c ? H(13) -0.8920 0.3805 -0.8883 0.072 1.000 . Uiso c ? H(14) -0.7529 -0.0707 -0.9091 0.061 1.000 . Uiso c ? H(15) -0.8418 -0.2251 -0.8716 0.080 1.000 . Uiso c ? H(16) -0.9689 -0.1220 -0.8625 0.080 1.000 . Uiso c ? H(17) -1.2146 -0.0629 -0.9159 0.114 1.000 . Uiso c ? H(18) -1.1866 -0.0273 -0.9527 0.114 1.000 . Uiso c ? H(19) -1.2265 -0.1845 -0.9422 0.114 1.000 . Uiso c ? H(20) -0.9956 -0.2930 -0.9651 0.117 1.000 . Uiso c ? H(21) -0.8496 -0.2166 -0.9569 0.117 1.000 . Uiso c ? H(22) -0.9622 -0.1404 -0.9795 0.117 1.000 . Uiso c ? H(23) -0.9014 0.1327 -0.8712 0.052 1.000 . Uiso c ? H(24) -0.7896 0.2326 -0.8248 0.062 1.000 . Uiso c ? H(25) -0.6292 0.2385 -0.8365 0.062 1.000 . Uiso c ? H(26) -0.5583 0.1474 -0.9223 0.070 1.000 . Uiso c ? H(27) -0.5470 0.3973 -0.9480 0.092 1.000 . Uiso c ? H(28) -0.7547 0.5382 -0.9260 0.093 1.000 . Uiso c ? H(29) -0.8209 -0.0036 -0.7848 0.091 1.000 . Uiso c ? H(30) -0.7564 -0.0711 -0.7324 0.103 1.000 . Uiso c ? H(31) -0.5421 0.0161 -0.7093 0.102 1.000 . Uiso c ? H(32) -0.3976 0.1758 -0.7391 0.102 1.000 . Uiso c ? H(33) -0.4641 0.2452 -0.7921 0.080 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.119(1) 0.0522(8) 0.086(1) -0.0436(9) -0.048(1) 0.0226(9) O(3) 0.0713(9) 0.0416(7) 0.0615(8) -0.0159(7) -0.0247(8) 0.0091(7) O(10) 0.0432(8) 0.0424(7) 0.081(1) 0.0049(7) -0.0042(7) 0.0018(8) N(1') 0.051(1) 0.0400(9) 0.089(1) 0.0059(9) 0.000(1) 0.007(1) N(9) 0.0407(9) 0.0396(9) 0.0580(9) 0.0012(7) -0.0072(9) -0.0023(9) C(1") 0.054(1) 0.046(1) 0.049(1) -0.004(1) -0.005(1) -0.003(1) C(2') 0.046(1) 0.035(1) 0.053(1) -0.0016(9) -0.003(1) 0.002(1) C(2) 0.075(2) 0.047(1) 0.064(1) -0.021(1) -0.025(1) 0.004(1) C(2") 0.068(2) 0.076(2) 0.085(2) -0.019(1) -0.021(1) 0.025(1) C(3') 0.053(1) 0.059(1) 0.062(1) -0.005(1) 0.004(1) 0.000(1) C(3") 0.092(2) 0.095(2) 0.069(2) -0.023(2) -0.015(2) 0.030(2) C(4') 0.065(2) 0.077(2) 0.089(2) -0.024(1) -0.002(1) 0.026(1) C(4) 0.055(1) 0.036(1) 0.060(1) -0.006(1) -0.010(1) 0.002(1) C(4") 0.103(2) 0.081(2) 0.071(2) -0.014(2) -0.029(2) 0.014(1) C(5) 0.088(2) 0.052(1) 0.061(1) -0.019(1) -0.025(1) 0.009(1) C(5') 0.071(2) 0.052(1) 0.109(2) -0.013(1) -0.014(2) 0.032(1) C(5") 0.092(2) 0.098(2) 0.064(1) -0.031(2) -0.029(1) 0.007(1) C(6) 0.071(2) 0.085(2) 0.128(2) -0.021(2) -0.030(2) 0.006(2) C(6") 0.069(2) 0.072(2) 0.059(1) -0.017(1) -0.011(1) 0.000(1) C(7) 0.129(3) 0.077(2) 0.086(2) -0.025(2) -0.008(2) -0.019(2) C(8) 0.042(1) 0.041(1) 0.047(1) -0.0009(9) -0.0042(9) -0.0010(9) C(11) 0.059(1) 0.043(1) 0.052(1) -0.002(1) -0.003(1) -0.005(1) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2438 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_all 0.0484 _refine_ls_wR_factor_ref 0.0484 _refine_ls_goodness_of_fit_all 1.565 _refine_ls_goodness_of_fit_ref 1.565 _refine_ls_shift/su_max 0.0105 _refine_ls_shift/su_mean 0.0013 _refine_diff_density_min -0.18 _refine_diff_density_max 0.19 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.422(2) . . yes O1 C5 1.415(2) . . yes O3 C2 1.416(2) . . yes O3 C4 1.423(2) . . yes O10 N9 1.468(2) . . yes O10 H12 1.06 . . no N1' C2' 1.365(2) . . yes N1' C5' 1.357(3) . . yes N1' H13 0.95 . . no N9 C8 1.476(2) . . yes N9 C11 1.467(2) . . yes C1" C2" 1.376(3) . . yes C1" C6" 1.380(3) . . yes C1" C11 1.495(3) . . yes C2' C3' 1.362(3) . . yes C2' C8 1.500(3) . . yes C2 C6 1.490(3) . . yes C2 C7 1.491(3) . . yes C2" C3" 1.359(3) . . yes C2" H29 0.95 . . no C3' C4' 1.405(3) . . yes C3' H26 0.95 . . no C3" C4" 1.370(4) . . yes C3" H30 0.95 . . no C4' C5' 1.352(3) . . yes C4' H27 0.95 . . no C4 C5 1.510(3) . . yes C4 C8 1.519(3) . . yes C4 H14 0.95 . . no C4" C5" 1.370(4) . . yes C4" H31 0.95 . . no C5 H15 0.95 . . no C5 H16 0.95 . . no C5' H28 0.95 . . no C5" C6" 1.383(3) . . yes C5" H32 0.95 . . no C6 H17 0.95 . . no C6 H18 0.95 . . no C6 H19 0.95 . . no C6" H33 0.95 . . no C7 H20 0.95 . . no C7 H21 0.95 . . no C7 H22 0.95 . . no C8 H23 0.95 . . no C11 H24 0.95 . . no C11 H25 0.95 . . no H15 H16 1.55 . . no H17 H18 1.55 . . no H17 H19 1.55 . . no H18 H19 1.55 . . no H20 H21 1.55 . . no H20 H22 1.55 . . no H21 H22 1.55 . . no H24 H25 1.55 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 109.8(2) . . . yes C2 O3 C4 107.6(1) . . . yes N9 O10 H12 105.5 . . . no C2' N1' C5' 110.0(2) . . . yes C2' N1' H13 125.0 . . . no C5' N1' H13 125.0 . . . no O10 N9 C8 105.8(1) . . . yes O10 N9 C11 105.9(1) . . . yes C8 N9 C11 111.5(1) . . . yes C2" C1" C6" 117.8(2) . . . yes C2" C1" C11 120.4(2) . . . yes C6" C1" C11 121.8(2) . . . yes N1' C2' C3' 106.4(2) . . . yes N1' C2' C8 121.1(2) . . . yes C3' C2' C8 132.5(2) . . . yes O1 C2 O3 105.6(2) . . . yes O1 C2 C6 109.6(2) . . . yes O1 C2 C7 108.8(2) . . . yes O3 C2 C6 108.0(2) . . . yes O3 C2 C7 110.9(2) . . . yes C6 C2 C7 113.7(2) . . . yes C1" C2" C3" 122.2(2) . . . yes C1" C2" H29 118.9 . . . no C3" C2" H29 118.9 . . . no C2' C3' C4' 108.6(2) . . . yes C2' C3' H26 125.7 . . . no C4' C3' H26 125.7 . . . no C2" C3" C4" 119.8(2) . . . yes C2" C3" H30 120.1 . . . no C4" C3" H30 120.1 . . . no C3' C4' C5' 106.8(2) . . . yes C3' C4' H27 126.6 . . . no C5' C4' H27 126.6 . . . no O3 C4 C5 102.2(2) . . . yes O3 C4 C8 108.4(2) . . . yes O3 C4 H14 110.5 . . . no C5 C4 C8 114.5(2) . . . yes C5 C4 H14 110.5 . . . no C8 C4 H14 110.5 . . . no C3" C4" C5" 119.4(2) . . . yes C3" C4" H31 120.3 . . . no C5" C4" H31 120.3 . . . no O1 C5 C4 103.6(2) . . . yes O1 C5 H15 110.9 . . . no O1 C5 H16 110.9 . . . no C4 C5 H15 110.9 . . . no C4 C5 H16 110.9 . . . no H15 C5 H16 109.5 . . . no N1' C5' C4' 108.2(2) . . . yes N1' C5' H28 125.9 . . . no C4' C5' H28 125.9 . . . no C4" C5" C6" 120.5(2) . . . yes C4" C5" H32 119.7 . . . no C6" C5" H32 119.7 . . . no C2 C6 H17 109.5 . . . no C2 C6 H18 109.5 . . . no C2 C6 H19 109.5 . . . no H17 C6 H18 109.5 . . . no H17 C6 H19 109.5 . . . no H18 C6 H19 109.5 . . . no C1" C6" C5" 120.2(2) . . . yes C1" C6" H33 119.9 . . . no C5" C6" H33 119.9 . . . no C2 C7 H20 109.5 . . . no C2 C7 H21 109.5 . . . no C2 C7 H22 109.5 . . . no H20 C7 H21 109.5 . . . no H20 C7 H22 109.5 . . . no H21 C7 H22 109.5 . . . no N9 C8 C2' 116.7(2) . . . yes N9 C8 C4 108.1(2) . . . yes N9 C8 H23 106.4 . . . no C2' C8 C4 112.1(2) . . . yes C2' C8 H23 106.4 . . . no C4 C8 H23 106.4 . . . no N9 C11 C1" 112.0(2) . . . yes N9 C11 H24 108.8 . . . no N9 C11 H25 108.8 . . . no C1" C11 H24 108.8 . . . no C1" C11 H25 108.8 . . . no H24 C11 H25 109.5 . . . no H18 H17 H19 60.0 . . . no H17 H18 H19 60.0 . . . no H17 H19 H18 60.0 . . . no H21 H20 H22 60.0 . . . no H20 H21 H22 60.0 . . . no H20 H22 H21 60.0 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O10 2.756(2) . 8_443 no O3 C6" 3.590(3) . 8_453 no O10 N1' 2.891(2) . 8_553 no O10 C5' 3.522(3) . 8_553 no O10 C5 3.598(3) . 8_543 no N1' C6" 3.487(3) . 8_453 no C5' C6" 3.538(4) . 8_453 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A O10 H12 O1 1.06 1.73 2.756(2) 160.5 8_543 N1' H13 O10 0.95 2.05 2.891(2) 146.1 8_453 # Attachment 'file11.cif.txt' data_ChristopheI _database_code_depnum_ccdc_archive 'CCDC 679402' #------------------------------------------------------------------------------ _computing_data_collection 'Bruker-Enraf-Nonius kappaCCD' _computing_cell_refinement 'Bruker-Enraf-Nonius kappaCCD' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 11.014(1) _cell_length_b 13.240(2) _cell_length_c 17.939(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2616.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description colorless _exptl_crystal_colour platelet _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 258.28 _chemical_formula_analytical ? _chemical_formula_sum 'C14 H14 N2 O3 ' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1088.00 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector CCD _diffrn_measurement_device_type 'Bruker-Enraf-Nonius kappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? _diffrn_reflns_number 25991 _reflns_number_total 5035 _reflns_number_gt 3378 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.09104 _diffrn_reflns_av_sigmaI/netI 0.240 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 31.99 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 112 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 112 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 16 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 24 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1a) 0.7904(2) 0.6053(1) 0.1440(1) 0.0349(4) 1.000 . Uani d ? O(1b) 0.7741(1) 0.1377(1) 0.14211(9) 0.0273(4) 1.000 . Uani d ? O(7a) 0.6930(2) 0.4145(1) 0.06922(9) 0.0290(4) 1.000 . Uani d ? O(7b) 0.5878(1) 0.2332(1) 0.0272(1) 0.0266(3) 1.000 . Uani d ? O(8a) 0.9720(2) 0.5890(1) 0.0970(1) 0.0398(5) 1.000 . Uani d ? O(8b) 0.9214(2) 0.1906(1) 0.0713(1) 0.0338(4) 1.000 . Uani d ? N(1'a) 0.9455(2) 0.3088(2) 0.2248(1) 0.0400(5) 1.000 . Uani d ? N(1'b) 0.7149(2) -0.0433(2) -0.0560(1) 0.0381(5) 1.000 . Uani d ? N(4b) 0.6146(2) 0.1270(1) 0.0161(1) 0.0229(4) 1.000 . Uani d ? N(4a) 0.7525(2) 0.3933(1) 0.1395(1) 0.0225(4) 1.000 . Uani d ? C(1"a) 0.5716(2) 0.4086(2) 0.2209(1) 0.0244(4) 1.000 . Uani d ? C(1"b) 0.4450(2) 0.0713(2) 0.0962(1) 0.0282(5) 1.000 . Uani d ? C(2"a) 0.5744(2) 0.3384(2) 0.2787(1) 0.0301(5) 1.000 . Uani d ? C(2'a) 0.9495(2) 0.4053(2) 0.1982(1) 0.0272(5) 1.000 . Uani d ? C(2b) 0.8203(2) 0.1555(2) 0.0749(1) 0.0259(4) 1.000 . Uani d ? C(2'b) 0.7873(2) 0.0195(2) -0.0150(1) 0.0277(5) 1.000 . Uani d ? C(2a) 0.8822(2) 0.5479(2) 0.1217(1) 0.0298(5) 1.000 . Uani d ? C(2"b) 0.3823(2) -0.0154(2) 0.0759(1) 0.0338(5) 1.000 . Uani d ? C(3b) 0.7482(2) 0.1238(2) 0.0060(1) 0.0256(4) 1.000 . Uani d ? C(3"a) 0.4701(3) 0.2970(2) 0.3074(2) 0.0383(6) 1.000 . Uani d ? C(3'b) 0.8939(2) -0.0323(2) 0.0004(1) 0.0355(6) 1.000 . Uani d ? C(3a) 0.8766(2) 0.4334(2) 0.1308(1) 0.0252(4) 1.000 . Uani d ? C(3'a) 1.0191(2) 0.4614(2) 0.2470(2) 0.0358(6) 1.000 . Uani d ? C(3"b) 0.2567(3) -0.0210(2) 0.0851(2) 0.0444(7) 1.000 . Uani d ? C(4'a) 1.0568(2) 0.3958(3) 0.3044(2) 0.0410(6) 1.000 . Uani d ? C(4"a) 0.3574(2) 0.3249(2) 0.2788(2) 0.0366(6) 1.000 . Uani d ? C(4'b) 0.8823(3) -0.1297(2) -0.0321(2) 0.0455(7) 1.000 . Uani d ? C(4"b) 0.1929(2) 0.0597(3) 0.1148(2) 0.0447(7) 1.000 . Uani d ? C(5"a) 0.3522(2) 0.3933(2) 0.2203(2) 0.0367(6) 1.000 . Uani d ? C(5b) 0.5813(2) 0.0751(2) 0.0862(1) 0.0246(4) 1.000 . Uani d ? C(5'b) 0.7708(3) -0.1340(3) -0.0660(2) 0.0503(8) 1.000 . Uani d ? C(5a) 0.6892(2) 0.4552(2) 0.1964(1) 0.0238(4) 1.000 . Uani d ? C(5'a) 1.0108(3) 0.3026(3) 0.2898(2) 0.0470(7) 1.000 . Uani d ? C(5"b) 0.2537(2) 0.1459(3) 0.1345(2) 0.0432(7) 1.000 . Uani d ? C(6"a) 0.4589(2) 0.4353(2) 0.1914(1) 0.0300(5) 1.000 . Uani d ? C(6a) 0.6761(2) 0.5629(2) 0.1696(2) 0.0310(5) 1.000 . Uani d ? C(6b) 0.6439(2) 0.1226(2) 0.1530(1) 0.0295(5) 1.000 . Uani d ? C(6"b) 0.3800(2) 0.1528(2) 0.1253(2) 0.0362(6) 1.000 . Uani d ? H(1a) 0.6684 0.3563 0.0576 0.051 1.000 . Uiso c ? H(1b) 0.5321 0.2487 -0.0030 0.051 1.000 . Uiso c ? H(2a) 0.9038 0.2542 0.2019 0.048 1.000 . Uiso c ? H(2b) 0.6368 -0.0262 -0.0746 0.046 1.000 . Uiso c ? H(3a) 0.9126 0.4029 0.0882 0.030 1.000 . Uiso c ? H(3b) 0.7688 0.1681 -0.0336 0.031 1.000 . Uiso c ? H(4a) 0.7405 0.4570 0.2390 0.029 1.000 . Uiso c ? H(4b) 0.6093 0.0074 0.0825 0.029 1.000 . Uiso c ? H(5a) 0.6464 0.6030 0.2095 0.037 1.000 . Uiso c ? H(5b) 0.6075 0.1863 0.1625 0.035 1.000 . Uiso c ? H(6a) 0.6197 0.5643 0.1296 0.037 1.000 . Uiso c ? H(6b) 0.6325 0.0798 0.1949 0.035 1.000 . Uiso c ? H(7a) 1.0380 0.5311 0.2427 0.043 1.000 . Uiso c ? H(7b) 0.9616 -0.0074 0.0275 0.043 1.000 . Uiso c ? H(8a) 1.1058 0.4135 0.3459 0.049 1.000 . Uiso c ? H(8b) 0.9410 -0.1822 -0.0306 0.055 1.000 . Uiso c ? H(9a) 1.0218 0.2437 0.3193 0.056 1.000 . Uiso c ? H(9b) 0.7383 -0.1903 -0.0920 0.060 1.000 . Uiso c ? H(10a) 0.6505 0.3186 0.2989 0.036 1.000 . Uiso c ? H(10b) 0.4253 -0.0712 0.0556 0.041 1.000 . Uiso c ? H(11a) 0.4748 0.2492 0.3468 0.046 1.000 . Uiso c ? H(11b) 0.2147 -0.0807 0.0710 0.053 1.000 . Uiso c ? H(12a) 0.2849 0.2974 0.2992 0.044 1.000 . Uiso c ? H(12b) 0.1075 0.0553 0.1214 0.054 1.000 . Uiso c ? H(13a) 0.2758 0.4118 0.1998 0.044 1.000 . Uiso c ? H(13b) 0.2101 0.2015 0.1546 0.052 1.000 . Uiso c ? H(14a) 0.4546 0.4821 0.1514 0.036 1.000 . Uiso c ? H(14b) 0.4213 0.2130 0.1388 0.043 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1a) 0.0321(8) 0.0224(7) 0.050(1) -0.0020(7) 0.0079(8) -0.0030(8) O(1b) 0.0239(7) 0.0340(8) 0.0241(7) -0.0021(6) -0.0025(6) 0.0012(7) O(7a) 0.0370(8) 0.0266(7) 0.0235(7) -0.0019(7) -0.0075(7) 0.0023(6) O(7b) 0.0258(7) 0.0226(6) 0.0314(7) 0.0011(6) -0.0033(6) 0.0006(6) O(8a) 0.0381(9) 0.0318(8) 0.050(1) -0.0083(8) 0.0132(8) -0.0057(8) O(8b) 0.0240(7) 0.0372(8) 0.0401(9) -0.0065(7) 0.0021(7) -0.0017(8) N(1'a) 0.043(1) 0.033(1) 0.044(1) 0.006(1) -0.018(1) -0.0007(9) N(1'b) 0.036(1) 0.041(1) 0.038(1) 0.007(1) -0.0072(9) -0.0128(9) N(4b) 0.0224(7) 0.0234(8) 0.0230(7) -0.0014(7) 0.0025(7) 0.0021(7) N(4a) 0.0243(7) 0.0232(7) 0.0199(7) 0.0011(7) -0.0042(6) -0.0011(7) C(1"a) 0.0243(8) 0.0252(9) 0.0237(8) 0.0002(8) -0.0005(7) -0.0039(8) C(1"b) 0.0250(9) 0.034(1) 0.0257(9) -0.0043(9) 0.0016(8) 0.0079(8) C(2"a) 0.032(1) 0.029(1) 0.029(1) -0.0032(9) -0.0080(9) -0.0004(9) C(2'a) 0.0205(8) 0.029(1) 0.032(1) 0.0062(8) -0.0015(8) -0.0044(9) C(2b) 0.0241(8) 0.0238(9) 0.030(1) -0.0001(8) 0.0003(8) 0.0014(8) C(2'b) 0.0245(8) 0.036(1) 0.0225(9) 0.0053(9) 0.0011(8) -0.0029(9) C(2a) 0.032(1) 0.0261(9) 0.031(1) -0.0025(9) 0.0026(9) -0.0027(9) C(2"b) 0.032(1) 0.037(1) 0.032(1) -0.009(1) -0.0029(9) 0.009(1) C(3b) 0.0208(8) 0.033(1) 0.0235(9) -0.0005(9) 0.0028(7) 0.0014(8) C(3"a) 0.045(1) 0.034(1) 0.036(1) -0.013(1) -0.002(1) 0.005(1) C(3'b) 0.029(1) 0.045(1) 0.032(1) 0.011(1) -0.0018(9) -0.001(1) C(3a) 0.0233(8) 0.0248(9) 0.0275(9) 0.0007(8) 0.0029(8) -0.0036(8) C(3'a) 0.026(1) 0.044(1) 0.038(1) 0.001(1) 0.000(1) -0.011(1) C(3"b) 0.037(1) 0.057(2) 0.040(1) -0.022(1) -0.011(1) 0.018(1) C(4'a) 0.027(1) 0.059(2) 0.037(1) 0.010(1) -0.005(1) -0.014(1) C(4"a) 0.029(1) 0.035(1) 0.045(1) -0.007(1) 0.009(1) -0.006(1) C(4'b) 0.045(1) 0.046(1) 0.046(1) 0.017(1) 0.001(1) -0.011(1) C(4"b) 0.025(1) 0.077(2) 0.032(1) -0.011(1) -0.0014(9) 0.014(1) C(5"a) 0.0244(9) 0.036(1) 0.050(1) 0.004(1) 0.001(1) -0.002(1) C(5b) 0.0242(8) 0.0255(9) 0.0240(9) -0.0016(8) 0.0013(8) 0.0036(8) C(5'b) 0.053(2) 0.046(1) 0.051(2) 0.011(1) -0.004(1) -0.021(1) C(5a) 0.0220(8) 0.0239(9) 0.0256(9) 0.0019(8) -0.0008(8) -0.0033(8) C(5'a) 0.048(1) 0.050(1) 0.043(1) 0.014(1) -0.016(1) 0.000(1) C(5"b) 0.0236(9) 0.070(2) 0.036(1) 0.001(1) 0.004(1) 0.002(1) C(6"a) 0.0228(8) 0.032(1) 0.035(1) 0.0016(9) 0.0019(9) 0.003(1) C(6a) 0.0261(9) 0.024(1) 0.043(1) 0.0022(9) 0.005(1) -0.0025(9) C(6b) 0.0244(9) 0.038(1) 0.0257(9) -0.0017(9) 0.0017(8) 0.0017(9) C(6"b) 0.0238(9) 0.048(1) 0.037(1) -0.001(1) 0.0064(9) -0.004(1) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo)]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3378 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_all 0.0734 _refine_ls_wR_factor_ref 0.0734 _refine_ls_goodness_of_fit_all 0.739 _refine_ls_goodness_of_fit_ref 0.739 _refine_ls_shift/su_max 0.0031 _refine_ls_shift/su_mean 0.0005 _refine_diff_density_min -0.22 _refine_diff_density_max 0.33 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1a C2a 1.326(3) . . yes O1a C6a 1.453(3) . . yes O1b C2b 1.329(3) . . yes O1b C6b 1.460(3) . . yes O7a N4a 1.449(2) . . yes O7a H1a 0.84 . . no O7b N4b 1.451(2) . . yes O7b H1b 0.84 . . no O8a C2a 1.213(3) . . yes O8b C2b 1.209(3) . . yes N1'a C2'a 1.365(3) . . yes N1'a C5'a 1.372(4) . . yes N1'a H2a 0.95 . . no N1'b C2'b 1.366(3) . . yes N1'b C5'b 1.361(4) . . yes N1'b H2b 0.95 . . no N4b C3b 1.482(3) . . yes N4b C5b 1.479(3) . . yes N4a C3a 1.475(3) . . yes N4a C5a 1.482(3) . . yes C1"a C2"a 1.393(3) . . yes C1"a C5a 1.501(3) . . yes C1"a C6"a 1.395(3) . . yes C1"b C2"b 1.388(4) . . yes C1"b C5b 1.513(3) . . yes C1"b C6"b 1.395(4) . . yes C2"a C3"a 1.372(4) . . yes C2"a H10a 0.95 . . no C2'a C3a 1.499(3) . . yes C2'a C3'a 1.380(4) . . yes C2b C3b 1.528(3) . . yes C2'b C3b 1.496(3) . . yes C2'b C3'b 1.387(3) . . yes C2a C3a 1.526(3) . . yes C2"b C3"b 1.395(4) . . yes C2"b H10b 0.95 . . no C3b H3b 0.95 . . no C3"a C4"a 1.393(4) . . yes C3"a H11a 0.95 . . no C3'b C4'b 1.421(4) . . yes C3'b H7b 0.95 . . no C3a H3a 0.95 . . no C3'a C4'a 1.410(4) . . yes C3'a H7a 0.95 . . no C3"b C4"b 1.385(5) . . yes C3"b H11b 0.95 . . no C4'a C5'a 1.359(5) . . yes C4'a H8a 0.95 . . no C4"a C5"a 1.388(4) . . yes C4"a H12a 0.95 . . no C4'b C5'b 1.372(5) . . yes C4'b H8b 0.95 . . no C4"b C5"b 1.370(5) . . yes C4"b H12b 0.95 . . no C5"a C6"a 1.400(4) . . yes C5"a H13a 0.95 . . no C5b C6b 1.520(3) . . yes C5b H4b 0.95 . . no C5'b H9b 0.95 . . no C5a C6a 1.512(3) . . yes C5a H4a 0.95 . . no C5'a H9a 0.95 . . no C5"b C6"b 1.404(3) . . yes C5"b H13b 0.95 . . no C6"a H14a 0.95 . . no C6a H5a 0.95 . . no C6a H6a 0.95 . . no C6b H5b 0.95 . . no C6b H6b 0.95 . . no C6"b H14b 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2a O1a C6a 122.3(2) . . . yes C2b O1b C6b 121.4(2) . . . yes N4a O7a H1a 100.6 . . . no N4b O7b H1b 107.3 . . . no C2'a N1'a C5'a 109.6(2) . . . yes C2'a N1'a H2a 125.2 . . . no C5'a N1'a H2a 125.2 . . . no C2'b N1'b C5'b 110.1(2) . . . yes C2'b N1'b H2b 124.9 . . . no C5'b N1'b H2b 124.9 . . . no O7b N4b C3b 104.3(2) . . . yes O7b N4b C5b 106.5(2) . . . yes C3b N4b C5b 109.7(2) . . . yes O7a N4a C3a 104.9(2) . . . yes O7a N4a C5a 106.2(2) . . . yes C3a N4a C5a 108.1(2) . . . yes C2"a C1"a C5a 118.3(2) . . . yes C2"a C1"a C6"a 118.1(2) . . . yes C5a C1"a C6"a 123.5(2) . . . yes C2"b C1"b C5b 119.3(2) . . . yes C2"b C1"b C6"b 118.8(2) . . . yes C5b C1"b C6"b 121.9(2) . . . yes C1"a C2"a C3"a 121.8(2) . . . yes C1"a C2"a H10a 119.1 . . . no C3"a C2"a H10a 119.1 . . . no N1'a C2'a C3a 119.9(2) . . . yes N1'a C2'a C3'a 107.4(2) . . . yes C3a C2'a C3'a 132.5(2) . . . yes O1b C2b O8b 118.0(2) . . . yes O1b C2b C3b 119.1(2) . . . yes O8b C2b C3b 122.7(2) . . . yes N1'b C2'b C3b 122.0(2) . . . yes N1'b C2'b C3'b 107.5(2) . . . yes C3b C2'b C3'b 130.5(2) . . . yes O1a C2a O8a 118.3(2) . . . yes O1a C2a C3a 120.4(2) . . . yes O8a C2a C3a 121.2(2) . . . yes C1"b C2"b C3"b 120.4(3) . . . yes C1"b C2"b H10b 119.8 . . . no C3"b C2"b H10b 119.8 . . . no N4b C3b C2b 114.1(2) . . . yes N4b C3b C2'b 110.0(2) . . . yes N4b C3b H3b 108.2 . . . no C2b C3b C2'b 108.0(2) . . . yes C2b C3b H3b 108.2 . . . no C2'b C3b H3b 108.2 . . . no C2"a C3"a C4"a 120.2(2) . . . yes C2"a C3"a H11a 119.9 . . . no C4"a C3"a H11a 119.9 . . . no C2'b C3'b C4'b 106.9(2) . . . yes C2'b C3'b H7b 126.6 . . . no C4'b C3'b H7b 126.6 . . . no N4a C3a C2'a 108.7(2) . . . yes N4a C3a C2a 114.0(2) . . . yes N4a C3a H3a 108.6 . . . no C2'a C3a C2a 108.2(2) . . . yes C2'a C3a H3a 108.6 . . . no C2a C3a H3a 108.6 . . . no C2'a C3'a C4'a 107.2(3) . . . yes C2'a C3'a H7a 126.4 . . . no C4'a C3'a H7a 126.4 . . . no C2"b C3"b C4"b 120.5(3) . . . yes C2"b C3"b H11b 119.8 . . . no C4"b C3"b H11b 119.8 . . . no C3'a C4'a C5'a 108.0(2) . . . yes C3'a C4'a H8a 126.0 . . . no C5'a C4'a H8a 126.0 . . . no C3"a C4"a C5"a 119.2(2) . . . yes C3"a C4"a H12a 120.4 . . . no C5"a C4"a H12a 120.4 . . . no C3'b C4'b C5'b 107.5(3) . . . yes C3'b C4'b H8b 126.3 . . . no C5'b C4'b H8b 126.3 . . . no C3"b C4"b C5"b 119.6(2) . . . yes C3"b C4"b H12b 120.2 . . . no C5"b C4"b H12b 120.2 . . . no C4"a C5"a C6"a 120.3(2) . . . yes C4"a C5"a H13a 119.8 . . . no C6"a C5"a H13a 119.8 . . . no N4b C5b C1"b 111.3(2) . . . yes N4b C5b C6b 111.5(2) . . . yes N4b C5b H4b 107.4 . . . no C1"b C5b C6b 111.7(2) . . . yes C1"b C5b H4b 107.4 . . . no C6b C5b H4b 107.4 . . . no N1'b C5'b C4'b 108.0(3) . . . yes N1'b C5'b H9b 126.0 . . . no C4'b C5'b H9b 126.0 . . . no N4a C5a C1"a 112.4(2) . . . yes N4a C5a C6a 110.3(2) . . . yes N4a C5a H4a 106.7 . . . no C1"a C5a C6a 113.5(2) . . . yes C1"a C5a H4a 106.7 . . . no C6a C5a H4a 106.7 . . . no N1'a C5'a C4'a 107.8(3) . . . yes N1'a C5'a H9a 126.1 . . . no C4'a C5'a H9a 126.1 . . . no C4"b C5"b C6"b 120.5(3) . . . yes C4"b C5"b H13b 119.7 . . . no C6"b C5"b H13b 119.7 . . . no C1"a C6"a C5"a 120.4(2) . . . yes C1"a C6"a H14a 119.8 . . . no C5"a C6"a H14a 119.8 . . . no O1a C6a C5a 112.5(2) . . . yes O1a C6a H5a 108.7 . . . no O1a C6a H6a 108.7 . . . no C5a C6a H5a 108.7 . . . no C5a C6a H6a 108.7 . . . no H5a C6a H6a 109.5 . . . no O1b C6b C5b 113.3(2) . . . yes O1b C6b H5b 108.5 . . . no O1b C6b H6b 108.5 . . . no C5b C6b H5b 108.5 . . . no C5b C6b H6b 108.5 . . . no H5b C6b H6b 109.5 . . . no C1"b C6"b C5"b 120.2(3) . . . yes C1"b C6"b H14b 119.9 . . . no C5"b C6"b H14b 119.9 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1b N1'a 3.301(3) . . no O1b N4a 3.393(3) . . no O7a O7b 2.770(2) . . no O7a C3"b 3.186(3) . 3 no O7a C4"b 3.318(3) . 3 no O7a C2"b 3.593(3) . 3 no O7b O8b 2.738(2) . 3_455 no O7b N4a 3.442(2) . . no O8a N1'b 2.840(3) . 3 no O8a C5'b 3.390(4) . 3 no O8a C2"b 3.398(4) . 3 no O8a C5'a 3.487(4) . 4_755 no O8b N1'a 3.178(3) . . no O8b C3a 3.423(3) . . no O8b N4a 3.487(3) . . no O8b C4"b 3.543(4) . 1_655 no O8b N4b 3.581(3) . 3 no N4a C2b 3.437(3) . . no C2"a C2"b 3.283(4) . 4_655 no C2"a C3"b 3.590(4) . 4_655 no C2a C2"b 3.570(4) . 3 no C3"a C6a 3.517(4) . 4_645 no C4'a C4"a 3.471(4) . 1_655 no C4'a C5"a 3.586(4) . 1_655 no C4"a C6"b 3.584(4) . . no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A O7a H1a O7b 0.84 1.94 2.770(2) 170.9 . O7b H1b O8b 0.84 1.90 2.738(2) 168.7 3_455 N1'b H2b O8a 0.95 2.04 2.840(3) 141.1 3_455 # Attachment 'file17.cif.txt' data_Demacle70/30_300_raies_eli _database_code_depnum_ccdc_archive 'CCDC 679403' #------------------------------------------------------------------------------ _computing_data_collection 'Bruker-Enraf-Nonius kappaCCD' _computing_cell_refinement 'Bruker-Enraf-Nonius kappaCCD' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 5.960(1) _cell_length_b 12.835(2) _cell_length_c 16.626(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1271.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293.0 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description block _exptl_crystal_colour brownish _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 258.28 _chemical_formula_analytical ? _chemical_formula_sum 'C14 H14 N2 O3 ' _chemical_formula_moiety 'C14 H14 N2 O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 544.00 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; The crystal was a twin with a 70/30 % ratio. The main lattice was deconvoluted from the other leading to the reject of 300 too much overlapped relections. ; _diffrn_ambient_temperature 293.0 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector CCD _diffrn_measurement_device_type 'Bruker-Enraf-Nonius kappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? _diffrn_reflns_number 8977 _reflns_number_total 1791 _reflns_number_gt 1128 _reflns_threshold_expression I>2.50\s(I) _diffrn_reflns_av_R_equivalents 0.11158 _diffrn_reflns_av_sigmaI/netI 0.100 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.49 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 56 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 56 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 12 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 1.3360(3) -0.1254(2) 0.5615(1) 0.0484(6) 1.000 . Uani d ? O(7) 0.8259(3) -0.1420(1) 0.5656(1) 0.0392(5) 1.000 . Uani d ? O(8) 1.3572(4) -0.2115(2) 0.6740(2) 0.0651(7) 1.000 . Uani d ? N(1') 1.3505(5) 0.1226(2) 0.7766(2) 0.0638(8) 1.000 . Uani d ? N(4) 0.9079(3) -0.0485(2) 0.6046(1) 0.0296(5) 1.000 . Uani d ? C(1") 0.8959(4) 0.0670(2) 0.4852(2) 0.0322(6) 1.000 . Uani d ? C(2') 1.3515(5) 0.0424(3) 0.7218(2) 0.0505(8) 1.000 . Uani d ? C(2) 1.2580(5) -0.1474(2) 0.6350(2) 0.0410(7) 1.000 . Uani d ? C(2") 0.6913(5) 0.1079(2) 0.5101(2) 0.0418(7) 1.000 . Uani d ? C(3) 1.0607(5) -0.0871(2) 0.6679(2) 0.0340(6) 1.000 . Uani d ? C(3') 1.1409(5) 0.0013(2) 0.7201(2) 0.0373(7) 1.000 . Uani d ? C(3") 0.5633(5) 0.1707(3) 0.4599(2) 0.0466(8) 1.000 . Uani d ? C(4') 1.0101(6) 0.0572(2) 0.7746(2) 0.0512(9) 1.000 . Uani d ? C(4") 0.6397(6) 0.1940(2) 0.3839(2) 0.0546(9) 1.000 . Uani d ? C(5) 1.0416(4) 0.0080(2) 0.5436(1) 0.0301(6) 1.000 . Uani d ? C(5') 1.1436(7) 0.1320(2) 0.8082(2) 0.062(1) 1.000 . Uani d ? C(5") 0.8408(7) 0.1558(3) 0.3586(2) 0.059(1) 1.000 . Uani d ? C(6) 1.2057(5) -0.0657(2) 0.5036(2) 0.0429(8) 1.000 . Uani d ? C(6") 0.9696(6) 0.0915(3) 0.4078(2) 0.0455(8) 1.000 . Uani d ? H(9) 0.6881 -0.1317 0.5463 0.067 1.000 . Uiso c ? H(10) 1.4761 0.1647 0.7900 0.077 1.000 . Uiso c ? H(11) 0.9771 -0.1331 0.7011 0.041 1.000 . Uiso c ? H(12) 1.1283 0.0584 0.5718 0.036 1.000 . Uiso c ? H(13) 1.3057 -0.0262 0.4712 0.051 1.000 . Uiso c ? H(14) 1.1241 -0.1127 0.4706 0.051 1.000 . Uiso c ? H(15) 1.4763 0.0197 0.6909 0.061 1.000 . Uiso c ? H(16) 0.8561 0.0454 0.7863 0.061 1.000 . Uiso c ? H(17) 1.0983 0.1820 0.8471 0.074 1.000 . Uiso c ? H(18) 0.6379 0.0926 0.5626 0.050 1.000 . Uiso c ? H(19) 0.4235 0.1974 0.4780 0.056 1.000 . Uiso c ? H(20) 0.5525 0.2367 0.3492 0.066 1.000 . Uiso c ? H(21) 0.8941 0.1732 0.3064 0.070 1.000 . Uiso c ? H(22) 1.1079 0.0643 0.3887 0.055 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0381(9) 0.052(1) 0.055(1) 0.015(1) 0.001(1) 0.003(1) O(7) 0.0393(9) 0.0311(9) 0.047(1) -0.0063(9) -0.0097(9) -0.0036(9) O(8) 0.068(2) 0.052(1) 0.075(2) 0.025(1) -0.015(1) 0.012(1) N(1') 0.093(2) 0.042(1) 0.056(2) -0.024(2) -0.039(2) 0.011(1) N(4) 0.032(1) 0.028(1) 0.029(1) -0.004(1) -0.006(1) 0.0002(9) C(1") 0.040(1) 0.025(1) 0.031(1) -0.006(1) -0.004(1) 0.001(1) C(2') 0.065(2) 0.051(2) 0.035(1) -0.017(2) -0.013(1) 0.007(1) C(2) 0.042(1) 0.031(1) 0.051(2) 0.002(1) -0.010(1) 0.001(1) C(2") 0.044(1) 0.034(1) 0.047(2) 0.001(1) -0.001(1) 0.006(1) C(3) 0.041(1) 0.025(1) 0.036(1) -0.002(1) -0.005(1) 0.006(1) C(3') 0.050(2) 0.030(1) 0.032(1) -0.003(1) -0.011(1) 0.009(1) C(3") 0.046(2) 0.038(1) 0.055(2) 0.008(1) -0.008(2) 0.004(1) C(4') 0.059(2) 0.041(2) 0.054(2) 0.007(2) -0.010(2) -0.010(1) C(4") 0.077(2) 0.039(2) 0.048(2) 0.007(2) -0.020(2) 0.007(1) C(5) 0.028(1) 0.035(1) 0.027(1) -0.004(1) -0.001(1) -0.001(1) C(5') 0.099(3) 0.034(1) 0.052(2) 0.015(2) -0.028(2) -0.004(1) C(5") 0.088(3) 0.054(2) 0.034(1) 0.001(2) -0.007(2) 0.009(2) C(6) 0.039(2) 0.051(2) 0.038(1) 0.003(1) 0.001(1) 0.000(1) C(6") 0.055(2) 0.047(2) 0.034(1) 0.007(2) 0.001(1) 0.002(1) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo)]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1128 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_all 0.0620 _refine_ls_wR_factor_ref 0.0620 _refine_ls_goodness_of_fit_all 1.512 _refine_ls_goodness_of_fit_ref 1.512 _refine_ls_shift/su_max 0.0025 _refine_ls_shift/su_mean 0.0003 _refine_diff_density_min -0.25 _refine_diff_density_max 0.30 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.338(4) . . yes O1 C6 1.455(4) . . yes O7 N4 1.449(3) . . yes O7 H9 0.89 . . no O8 C2 1.202(4) . . yes N1' C2' 1.374(4) . . yes N1' C5' 1.347(5) . . yes N1' H10 0.95 . . no N4 C3 1.477(3) . . yes N4 C5 1.479(3) . . yes C1" C2" 1.391(4) . . yes C1" C5 1.507(4) . . yes C1" C6" 1.395(4) . . yes C2' C3' 1.361(4) . . yes C2' H15 0.95 . . no C2 C3 1.511(4) . . yes C2" C3" 1.388(4) . . yes C2" H18 0.95 . . no C3 C3' 1.506(4) . . yes C3 H11 0.95 . . no C3' C4' 1.395(4) . . yes C3" C4" 1.376(5) . . yes C3" H19 0.95 . . no C4' C5' 1.366(5) . . yes C4' H16 0.95 . . no C4" C5" 1.362(5) . . yes C4" H20 0.95 . . no C5 C6 1.515(4) . . yes C5 H12 0.95 . . no C5' H17 0.95 . . no C5" C6" 1.393(4) . . yes C5" H21 0.95 . . no C6 H13 0.95 . . no C6 H14 0.95 . . no C6" H22 0.95 . . no H13 H14 1.55 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C6 122.0(2) . . . yes N4 O7 H9 110.3 . . . no C2' N1' C5' 109.3(3) . . . yes C2' N1' H10 125.4 . . . no C5' N1' H10 125.4 . . . no O7 N4 C3 104.4(2) . . . yes O7 N4 C5 106.4(2) . . . yes C3 N4 C5 108.7(2) . . . yes C2" C1" C5 120.2(2) . . . yes C2" C1" C6" 117.7(3) . . . yes C5 C1" C6" 121.8(2) . . . yes N1' C2' C3' 107.5(3) . . . yes N1' C2' H15 126.3 . . . no C3' C2' H15 126.3 . . . no O1 C2 O8 117.8(3) . . . yes O1 C2 C3 119.5(2) . . . yes O8 C2 C3 122.6(3) . . . yes C1" C2" C3" 121.5(3) . . . yes C1" C2" H18 119.3 . . . no C3" C2" H18 119.3 . . . no N4 C3 C2 113.2(2) . . . yes N4 C3 C3' 110.8(2) . . . yes N4 C3 H11 107.4 . . . no C2 C3 C3' 110.3(2) . . . yes C2 C3 H11 107.4 . . . no C3' C3 H11 107.4 . . . no C2' C3' C3 126.6(3) . . . yes C2' C3' C4' 107.6(3) . . . yes C3 C3' C4' 125.8(3) . . . yes C2" C3" C4" 119.8(3) . . . yes C2" C3" H19 120.1 . . . no C4" C3" H19 120.1 . . . no C3' C4' C5' 107.5(3) . . . yes C3' C4' H16 126.2 . . . no C5' C4' H16 126.2 . . . no C3" C4" C5" 119.8(3) . . . yes C3" C4" H20 120.1 . . . no C5" C4" H20 120.1 . . . no N4 C5 C1" 112.2(2) . . . yes N4 C5 C6 110.0(2) . . . yes N4 C5 H12 106.8 . . . no C1" C5 C6 113.7(2) . . . yes C1" C5 H12 106.8 . . . no C6 C5 H12 106.8 . . . no N1' C5' C4' 108.1(3) . . . yes N1' C5' H17 126.0 . . . no C4' C5' H17 126.0 . . . no C4" C5" C6" 121.1(3) . . . yes C4" C5" H21 119.4 . . . no C6" C5" H21 119.4 . . . no O1 C6 C5 112.5(2) . . . yes O1 C6 H13 108.7 . . . no O1 C6 H14 108.7 . . . no C5 C6 H13 108.7 . . . no C5 C6 H14 108.7 . . . no H13 C6 H14 109.5 . . . no C1" C6" C5" 120.1(3) . . . yes C1" C6" H22 119.9 . . . no C5" C6" H22 119.9 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O7 2.928(2) . 1_655 no O7 O8 3.441(3) . 1_455 no O7 C2 3.576(4) . 1_455 no O7 C5' 3.584(4) . 4_746 no O8 N1' 2.872(4) . 4_846 no C5' C6 3.476(4) . 2_755 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A N1' H10 O8 0.95 1.97 2.872(4) 158.3 4_856