data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Wentrup, Curt' 'Bernhardt, P.' 'Koch, Rainer' 'Moloney, Daniel W. J.' 'Shtaiwi, Majed A.' _publ_contact_author_name 'Prof Curt Wentrup' _publ_contact_author_address ; Department of Chemistry University of Queensland Brisbane Queensland 4072 AUSTRALIA ; _publ_contact_author_email 'WENTRUP@CHEMISTRY.UQ.EDU.AU' _publ_section_title ; Twisting and Planarization in push-pull ethylenes ; data_1091dm9 _database_code_CSD 177773 _audit_creation_date 2001-10-16T10:13:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C9 H12 N2 O4' _chemical_formula_weight 212.21 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3920(5) _cell_length_b 9.3030(5) _cell_length_c 10.4410(10) _cell_angle_alpha 99.628(6) _cell_angle_beta 94.446(8) _cell_angle_gamma 104.090(6) _cell_volume 496.98(7) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_T_min 0.9458 _exptl_absorpt_correction_T_max 0.9888 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 507(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 1930 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_unetI/netI 0.0418 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 1730 _reflns_number_gt 955 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0505P)^2^+0.0982P] 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_number_reflns 1730 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.119 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.03 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.151 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.4460(3) 0.89995(18) 0.69893(16) 0.0572(5) Uani 1 1 d . . . C2 C 0.2658(5) 0.7703(3) 0.6209(2) 0.0490(6) Uani 1 1 d . . . C21 C 0.1248(6) 0.8256(3) 0.5172(3) 0.0740(9) Uani 1 1 d . . . H21A H 0.245 0.8716 0.4633 0.111 Uiso 1 1 calc R . . H21B H 0.042 0.8986 0.5581 0.111 Uiso 1 1 calc R . . H21C H -0.0026 0.742 0.464 0.111 Uiso 1 1 calc R . . C22 C 0.4032(6) 0.6558(3) 0.5651(3) 0.0656(8) Uani 1 1 d . . . H22A H 0.5307 0.701 0.5143 0.098 Uiso 1 1 calc R . . H22B H 0.2811 0.571 0.5102 0.098 Uiso 1 1 calc R . . H22C H 0.4854 0.6224 0.6352 0.098 Uiso 1 1 calc R . . O3 O 0.0753(3) 0.70377(19) 0.69674(16) 0.0542(5) Uani 1 1 d . . . C4 C 0.1580(5) 0.6809(3) 0.8165(2) 0.0489(6) Uani 1 1 d . . . O4 O 0.0081(4) 0.5881(2) 0.86253(18) 0.0741(6) Uani 1 1 d . . . C5 C 0.4076(4) 0.7690(3) 0.8758(2) 0.0443(6) Uani 1 1 d . . . C6 C 0.5518(5) 0.8859(3) 0.8181(2) 0.0500(6) Uani 1 1 d . . . O6 O 0.7549(4) 0.9774(2) 0.86457(18) 0.0710(6) Uani 1 1 d . . . C7 C 0.5050(5) 0.7497(3) 1.0004(2) 0.0459(6) Uani 1 1 d . . . N2 N 0.3868(5) 0.6493(3) 1.0670(2) 0.0574(6) Uani 1 1 d . . . H2 H 0.240(6) 0.593(3) 1.037(3) 0.093(12) Uiso 1 1 d . . . C9 C 0.5274(6) 0.6624(4) 1.1933(3) 0.0698(9) Uani 1 1 d . . . H9A H 0.5555 0.5662 1.2055 0.084 Uiso 1 1 calc R . . H9B H 0.4374 0.6994 1.2633 0.084 Uiso 1 1 calc R . . C10 C 0.7788(5) 0.7755(3) 1.1878(3) 0.0658(8) Uani 1 1 d . . . H10A H 0.8187 0.8577 1.263 0.079 Uiso 1 1 calc R . . H10B H 0.9201 0.7279 1.1838 0.079 Uiso 1 1 calc R . . N1 N 0.7279(4) 0.8277(3) 1.0684(2) 0.0601(7) Uani 1 1 d . . . H1 H 0.831(5) 0.897(3) 1.040(3) 0.069(9) Uiso 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 O1 0.0616(12) 0.0501(10) 0.0542(11) 0.0198(8) -0.0054(9) 0.0009(9) C2 0.0437(14) 0.0559(15) 0.0457(14) 0.0174(12) -0.0005(12) 0.0068(12) C21 0.073(2) 0.080(2) 0.0689(19) 0.0300(16) -0.0119(16) 0.0144(16) C22 0.0663(18) 0.0747(19) 0.0574(17) 0.0116(14) 0.0092(14) 0.0215(16) O3 0.0372(9) 0.0726(12) 0.0503(10) 0.0195(9) -0.0020(8) 0.0064(8) C4 0.0403(14) 0.0576(16) 0.0465(15) 0.0126(12) 0.0031(12) 0.0076(12) O4 0.0475(11) 0.0953(15) 0.0681(13) 0.0362(11) 0.0007(10) -0.0144(10) C5 0.0397(13) 0.0478(14) 0.0428(14) 0.0108(11) 0.0021(11) 0.0061(11) C6 0.0517(16) 0.0503(15) 0.0459(15) 0.0150(12) 0.0012(13) 0.0069(13) O6 0.0608(12) 0.0644(12) 0.0697(13) 0.0235(10) -0.0127(10) -0.0185(10) C7 0.0438(14) 0.0474(15) 0.0425(14) 0.0092(12) 0.0046(12) 0.0043(12) N2 0.0528(14) 0.0627(14) 0.0499(13) 0.0203(11) 0.0015(11) -0.0028(12) C9 0.071(2) 0.088(2) 0.0471(16) 0.0242(15) 0.0015(15) 0.0079(17) C10 0.0680(19) 0.0725(19) 0.0536(17) 0.0193(14) -0.0064(15) 0.0116(16) N1 0.0517(14) 0.0673(15) 0.0505(13) 0.0205(12) -0.0084(11) -0.0067(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.368(3) . ? O1 C2 1.429(3) . ? C2 O3 1.430(3) . ? C2 C22 1.505(4) . ? C2 C21 1.505(3) . ? O3 C4 1.363(3) . ? C4 O4 1.220(3) . ? C4 C5 1.425(3) . ? C5 C7 1.420(3) . ? C5 C6 1.426(3) . ? C6 O6 1.218(3) . ? C7 N1 1.322(3) . ? C7 N2 1.326(3) . ? N2 C9 1.440(3) . ? C9 C10 1.512(4) . ? C10 N1 1.443(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 O1 C2 117.79(18) . . ? O1 C2 O3 110.68(19) . . ? O1 C2 C22 110.3(2) . . ? O3 C2 C22 109.8(2) . . ? O1 C2 C21 106.8(2) . . ? O3 C2 C21 106.2(2) . . ? C22 C2 C21 113.0(2) . . ? C4 O3 C2 117.76(18) . . ? O4 C4 O3 116.2(2) . . ? O4 C4 C5 126.8(2) . . ? O3 C4 C5 116.9(2) . . ? C7 C5 C4 119.6(2) . . ? C7 C5 C6 119.1(2) . . ? C4 C5 C6 121.1(2) . . ? O6 C6 O1 116.4(2) . . ? O6 C6 C5 127.3(2) . . ? O1 C6 C5 116.3(2) . . ? N1 C7 N2 108.9(2) . . ? N1 C7 C5 125.8(2) . . ? N2 C7 C5 125.3(2) . . ? C7 N2 C9 112.4(2) . . ? N2 C9 C10 102.8(2) . . ? N1 C10 C9 102.6(2) . . ? C7 N1 C10 112.6(2) . . ? 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 O1 C2 O3 48.8(3) . . . . ? C6 O1 C2 C22 -72.9(3) . . . . ? C6 O1 C2 C21 164.0(2) . . . . ? O1 C2 O3 C4 -47.5(3) . . . . ? C22 C2 O3 C4 74.5(3) . . . . ? C21 C2 O3 C4 -163.0(2) . . . . ? C2 O3 C4 O4 -159.8(2) . . . . ? C2 O3 C4 C5 21.2(3) . . . . ? O4 C4 C5 C7 1.4(4) . . . . ? O3 C4 C5 C7 -179.7(2) . . . . ? O4 C4 C5 C6 -172.7(3) . . . . ? O3 C4 C5 C6 6.1(4) . . . . ? C2 O1 C6 O6 158.4(2) . . . . ? C2 O1 C6 C5 -23.5(3) . . . . ? C7 C5 C6 O6 -1.4(4) . . . . ? C4 C5 C6 O6 172.8(3) . . . . ? C7 C5 C6 O1 -179.2(2) . . . . ? C4 C5 C6 O1 -5.0(4) . . . . ? C4 C5 C7 N1 -177.2(3) . . . . ? C6 C5 C7 N1 -2.9(4) . . . . ? C4 C5 C7 N2 3.3(4) . . . . ? C6 C5 C7 N2 177.5(3) . . . . ? N1 C7 N2 C9 3.5(3) . . . . ? C5 C7 N2 C9 -176.9(3) . . . . ? C7 N2 C9 C10 -8.0(3) . . . . ? N2 C9 C10 N1 8.8(3) . . . . ? N2 C7 N1 C10 3.0(3) . . . . ? C5 C7 N1 C10 -176.6(3) . . . . ? C9 C10 N1 C7 -7.7(3) . . . . ? #===END # Compound (9) # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-10-16 at 10:22:29 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 1074dm8 data_1074dm8 _database_code_CSD 177774 _audit_creation_date 2001-10-16T10:22:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C11 H16 N2 O4' _chemical_formula_weight 240.26 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.365(6) _cell_length_b 20.595(8) _cell_length_c 10.740(10) _cell_angle_alpha 90 _cell_angle_beta 97.69(5) _cell_angle_gamma 90 _cell_volume 1176.0(18) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_min 0.9402 _exptl_absorpt_correction_T_max 0.9498 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 2077 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.017 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2077 _reflns_number_gt 1657 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1750P)^2^+0.6539P] 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_number_reflns 2077 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.089 _refine_ls_R_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.2449 _refine_ls_wR_factor_gt 0.2329 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.454 _refine_diff_density_min -0.47 _refine_diff_density_rms 0.106 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.2724(4) 0.04797(9) 0.08533(18) 0.0381(6) Uani 1 1 d . . . C2 C 0.1664(6) 0.10105(14) 0.0110(3) 0.0353(7) Uani 1 1 d . . . O3 O 0.3116(4) 0.15896(10) 0.04273(18) 0.0384(6) Uani 1 1 d . . . C4 C 0.3752(6) 0.17385(14) 0.1675(3) 0.0321(7) Uani 1 1 d . . . O4 O 0.4455(4) 0.22924(10) 0.1923(2) 0.0440(7) Uani 1 1 d . . . C5 C 0.3623(5) 0.12240(13) 0.2542(2) 0.0286(7) Uani 1 1 d . . . C6 C 0.3184(6) 0.05694(13) 0.2132(3) 0.0333(7) Uani 1 1 d . . . O6 O 0.3220(5) 0.00847(10) 0.2786(2) 0.0499(7) Uani 1 1 d . . . C7 C 0.4094(5) 0.13680(12) 0.3866(3) 0.0293(7) Uani 1 1 d . . . N1 N 0.5813(5) 0.10833(12) 0.4692(2) 0.0388(7) Uani 1 1 d . . . N2 N 0.2866(5) 0.18200(12) 0.4415(2) 0.0361(7) Uani 1 1 d . . . C8 C 0.3956(7) 0.19061(16) 0.5722(3) 0.0466(9) Uani 1 1 d . . . H8A H 0.2671 0.1889 0.6277 0.056 Uiso 1 1 calc R . . H8B H 0.4842 0.2317 0.5842 0.056 Uiso 1 1 calc R . . C9 C 0.5737(8) 0.13450(17) 0.5955(3) 0.0489(9) Uani 1 1 d . . . H9A H 0.739 0.1489 0.6331 0.059 Uiso 1 1 calc R . . H9B H 0.5112 0.1024 0.6498 0.059 Uiso 1 1 calc R . . C10 C 0.7694(7) 0.06179(16) 0.4442(3) 0.0462(9) Uani 1 1 d . . . H10A H 0.8671 0.0491 0.5218 0.069 Uiso 1 1 calc R . . H10B H 0.8776 0.081 0.3901 0.069 Uiso 1 1 calc R . . H10C H 0.6885 0.0243 0.4039 0.069 Uiso 1 1 calc R . . C11 C 0.0781(7) 0.22037(15) 0.3846(3) 0.0435(8) Uani 1 1 d . . . H11A H 0.0246 0.2491 0.4462 0.065 Uiso 1 1 calc R . . H11B H -0.0584 0.1923 0.3527 0.065 Uiso 1 1 calc R . . H11C H 0.1289 0.2454 0.3169 0.065 Uiso 1 1 calc R . . C21 C 0.1956(8) 0.0863(2) -0.1230(3) 0.0532(9) Uani 1 1 d . . . H21A H 0.1244 0.1209 -0.176 0.08 Uiso 1 1 calc R . . H21B H 0.1102 0.0464 -0.1479 0.08 Uiso 1 1 calc R . . H21C H 0.371 0.0819 -0.1309 0.08 Uiso 1 1 calc R . . C22 C -0.1042(7) 0.11129(16) 0.0314(3) 0.0477(9) Uani 1 1 d . . . H22A H -0.1736 0.1471 -0.019 0.072 Uiso 1 1 calc R . . H22B H -0.1113 0.1206 0.1184 0.072 Uiso 1 1 calc R . . H22C H -0.1994 0.0727 0.0077 0.072 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 0.0605(14) 0.0284(11) 0.0222(11) -0.0044(8) -0.0069(9) 0.0068(9) C2 0.0457(17) 0.0306(15) 0.0264(15) 0.0012(11) -0.0069(12) -0.0003(12) O3 0.0538(14) 0.0379(12) 0.0202(10) 0.0068(8) -0.0068(9) -0.0088(10) C4 0.0404(16) 0.0295(15) 0.0237(14) 0.0041(11) -0.0060(11) -0.0031(12) O4 0.0650(15) 0.0277(11) 0.0358(12) 0.0069(9) -0.0061(10) -0.0117(10) C5 0.0429(16) 0.0219(13) 0.0190(13) 0.0013(10) -0.0029(11) 0.0019(12) C6 0.0484(17) 0.0246(14) 0.0240(15) -0.0018(11) -0.0051(12) 0.0038(12) O6 0.0864(18) 0.0234(11) 0.0355(13) 0.0063(9) -0.0081(12) -0.0018(11) C7 0.0410(16) 0.0196(13) 0.0250(14) 0.0018(10) -0.0042(11) -0.0028(11) N1 0.0536(16) 0.0351(14) 0.0234(13) 0.0016(10) -0.0103(11) 0.0108(11) N2 0.0534(16) 0.0280(12) 0.0236(13) -0.0054(9) -0.0075(11) 0.0045(11) C8 0.069(2) 0.0408(17) 0.0253(16) -0.0099(13) -0.0112(15) 0.0059(16) C9 0.074(2) 0.0435(19) 0.0244(16) -0.0019(13) -0.0121(15) 0.0072(16) C10 0.050(2) 0.0416(18) 0.0431(19) 0.0053(14) -0.0061(15) 0.0118(15) C11 0.060(2) 0.0347(16) 0.0328(17) -0.0048(13) -0.0065(14) 0.0122(15) C21 0.067(2) 0.065(2) 0.0239(16) -0.0056(16) -0.0049(14) -0.0071(19) C22 0.0479(19) 0.0416(19) 0.049(2) -0.0026(15) -0.0097(16) -0.0019(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.375(4) . ? O1 C2 1.427(4) . ? C2 O3 1.441(4) . ? C2 C21 1.499(5) . ? C2 C22 1.511(5) . ? O3 C4 1.373(4) . ? C4 O4 1.220(4) . ? C4 C5 1.418(4) . ? C5 C6 1.428(4) . ? C5 C7 1.441(4) . ? C6 O6 1.219(4) . ? C7 N2 1.324(4) . ? C7 N1 1.328(4) . ? N1 C10 1.443(4) . ? N1 C9 1.465(4) . ? N2 C11 1.437(4) . ? N2 C8 1.458(4) . ? C8 C9 1.499(5) . ? 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 O1 C2 117.5(2) . . ? O1 C2 O3 109.8(2) . . ? O1 C2 C21 107.2(3) . . ? O3 C2 C21 105.8(3) . . ? O1 C2 C22 110.2(3) . . ? O3 C2 C22 110.5(3) . . ? C21 C2 C22 113.2(3) . . ? C4 O3 C2 118.2(2) . . ? O4 C4 O3 116.8(2) . . ? O4 C4 C5 126.6(3) . . ? O3 C4 C5 116.5(2) . . ? C4 C5 C6 121.6(3) . . ? C4 C5 C7 118.4(2) . . ? C6 C5 C7 119.9(2) . . ? O6 C6 O1 116.9(2) . . ? O6 C6 C5 127.3(3) . . ? O1 C6 C5 115.8(2) . . ? N2 C7 N1 110.8(3) . . ? N2 C7 C5 123.5(3) . . ? N1 C7 C5 125.7(3) . . ? C7 N1 C10 127.5(3) . . ? C7 N1 C9 110.7(3) . . ? C10 N1 C9 121.6(3) . . ? C7 N2 C11 127.0(2) . . ? C7 N2 C8 110.8(2) . . ? C11 N2 C8 122.1(2) . . ? N2 C8 C9 103.4(2) . . ? N1 C9 C8 103.1(2) . . ? 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 O1 C2 O3 51.2(3) . . . . ? C6 O1 C2 C21 165.7(3) . . . . ? C6 O1 C2 C22 -70.7(3) . . . . ? O1 C2 O3 C4 -47.1(3) . . . . ? C21 C2 O3 C4 -162.6(3) . . . . ? C22 C2 O3 C4 74.6(3) . . . . ? C2 O3 C4 O4 -163.6(3) . . . . ? C2 O3 C4 C5 18.9(4) . . . . ? O4 C4 C5 C6 -169.1(3) . . . . ? O3 C4 C5 C6 8.1(4) . . . . ? O4 C4 C5 C7 7.3(5) . . . . ? O3 C4 C5 C7 -175.5(3) . . . . ? C2 O1 C6 O6 154.7(3) . . . . ? C2 O1 C6 C5 -26.6(4) . . . . ? C4 C5 C6 O6 174.1(3) . . . . ? C7 C5 C6 O6 -2.2(5) . . . . ? C4 C5 C6 O1 -4.3(4) . . . . ? C7 C5 C6 O1 179.3(3) . . . . ? C4 C5 C7 N2 54.6(4) . . . . ? C6 C5 C7 N2 -129.0(3) . . . . ? C4 C5 C7 N1 -124.1(3) . . . . ? C6 C5 C7 N1 52.3(4) . . . . ? N2 C7 N1 C10 -173.1(3) . . . . ? C5 C7 N1 C10 5.7(5) . . . . ? N2 C7 N1 C9 2.0(4) . . . . ? C5 C7 N1 C9 -179.2(3) . . . . ? N1 C7 N2 C11 -176.1(3) . . . . ? C5 C7 N2 C11 5.1(5) . . . . ? N1 C7 N2 C8 5.7(4) . . . . ? C5 C7 N2 C8 -173.2(3) . . . . ? C7 N2 C8 C9 -10.5(4) . . . . ? C11 N2 C8 C9 171.1(3) . . . . ? C7 N1 C9 C8 -8.3(4) . . . . ? C10 N1 C9 C8 167.1(3) . . . . ? N2 C8 C9 N1 10.7(4) . . . . ? #===END # Compound (10) # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-08-06 at 14:04:58 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : cw3170a psi_scan data_cw3170a _database_code_CSD 177775 _audit_creation_date 2001-08-06T14:04:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H14 N2 O4' _chemical_formula_sum 'C9 H14 N2 O4' _chemical_formula_weight 214.22 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'I 2/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 16.913(5) _cell_length_b 6.379(2) _cell_length_c 19.750(6) _cell_angle_alpha 90 _cell_angle_beta 90.46(2) _cell_angle_gamma 90 _cell_volume 2130.7(11) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_factor_muR 0.021 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; ? ; _exptl_absorpt_correction_T_min 0.9491 _exptl_absorpt_correction_T_max 0.9792 _exptl_absorpt_correction_T_ave 0.9448 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 1921 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_unetI/netI 0.0385 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1878 _reflns_number_gt 1184 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0617P)^2^+2.0327P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0010(7) _refine_ls_number_reflns 1878 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.275 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.18011(10) 0.2306(3) 0.08050(9) 0.0498(6) Uani 1 1 d . . . O4 O -0.02038(10) 0.0030(3) 0.15259(10) 0.0538(6) Uani 1 1 d . . . O3 O 0.04603(10) 0.1525(3) 0.07054(9) 0.0483(5) Uani 1 1 d . . . O6 O 0.24690(11) 0.1680(3) 0.17395(10) 0.0555(6) Uani 1 1 d . . . C4 C 0.04515(16) 0.0474(4) 0.13066(13) 0.0417(7) Uani 1 1 d . . . N1 N 0.16618(14) -0.0350(4) 0.27772(12) 0.0472(6) Uani 1 1 d . . . N2 N 0.08463(14) -0.2838(4) 0.23305(13) 0.0471(6) Uani 1 1 d . . . C6 C 0.18597(16) 0.1357(4) 0.14226(13) 0.0428(7) Uani 1 1 d . . . C5 C 0.11948(14) 0.0155(4) 0.16356(12) 0.0389(6) Uani 1 1 d . . . C2 C 0.11907(16) 0.1599(5) 0.03454(14) 0.0484(7) Uani 1 1 d . . . C7 C 0.12303(15) -0.1023(4) 0.22595(13) 0.0393(6) Uani 1 1 d . . . C8 C 0.18151(19) -0.1531(5) 0.33879(14) 0.0593(8) Uani 1 1 d . . . H8A H 0.2145 -0.0723 0.3687 0.089 Uiso 1 1 calc R . . H8B H 0.2078 -0.2817 0.3276 0.089 Uiso 1 1 calc R . . H8C H 0.1324 -0.1838 0.3607 0.089 Uiso 1 1 calc R . . C21 C 0.13918(17) -0.0505(5) 0.00517(15) 0.0592(9) Uani 1 1 d . . . H21A H 0.1882 -0.0411 -0.0187 0.089 Uiso 1 1 calc R . . H21B H 0.098 -0.0935 -0.0255 0.089 Uiso 1 1 calc R . . H21C H 0.1442 -0.1515 0.041 0.089 Uiso 1 1 calc R . . C22 C 0.1102(2) 0.3270(6) -0.01827(17) 0.0755(11) Uani 1 1 d . . . H22A H 0.1581 0.3372 -0.0438 0.113 Uiso 1 1 calc R . . H22B H 0.0997 0.4589 0.0032 0.113 Uiso 1 1 calc R . . H22C H 0.0671 0.2919 -0.0481 0.113 Uiso 1 1 calc R . . C9 C 0.0490(2) -0.4066(5) 0.17907(16) 0.0637(9) Uani 1 1 d . . . H9A H 0.0253 -0.5303 0.1978 0.096 Uiso 1 1 calc R . . H9B H 0.0889 -0.4461 0.1472 0.096 Uiso 1 1 calc R . . H9C H 0.0091 -0.3246 0.1565 0.096 Uiso 1 1 calc R . . H1 H 0.1909(17) 0.081(5) 0.2712(14) 0.049(9) Uiso 1 1 d . . . H2 H 0.0820(15) -0.326(4) 0.2709(14) 0.040(8) Uiso 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 O1 0.0544(12) 0.0548(12) 0.0402(10) 0.0043(9) -0.0040(8) -0.0179(10) O4 0.0381(10) 0.0689(14) 0.0546(12) -0.0087(10) 0.0072(9) -0.0016(10) O3 0.0425(11) 0.0566(13) 0.0459(11) 0.0019(10) -0.0020(8) 0.0042(9) O6 0.0497(12) 0.0663(14) 0.0503(12) -0.0012(10) -0.0097(9) -0.0206(10) C4 0.0431(15) 0.0433(16) 0.0387(14) -0.0069(13) 0.0010(12) -0.0005(13) N1 0.0540(15) 0.0444(15) 0.0430(13) 0.0018(12) -0.0061(11) -0.0097(12) N2 0.0610(16) 0.0418(15) 0.0386(14) -0.0037(12) 0.0011(12) -0.0101(12) C6 0.0486(16) 0.0406(16) 0.0391(15) -0.0061(12) -0.0024(12) -0.0075(13) C5 0.0383(14) 0.0396(15) 0.0387(14) -0.0033(12) -0.0007(11) -0.0050(12) C2 0.0471(16) 0.0573(19) 0.0407(15) -0.0001(14) -0.0044(12) -0.0070(14) C7 0.0386(14) 0.0362(15) 0.0430(15) -0.0075(12) 0.0031(12) -0.0023(12) C8 0.071(2) 0.058(2) 0.0485(18) 0.0053(15) -0.0122(15) -0.0009(16) C21 0.0504(18) 0.076(2) 0.0510(18) -0.0150(17) -0.0005(14) -0.0049(16) C22 0.082(2) 0.085(3) 0.059(2) 0.023(2) -0.0088(18) -0.013(2) C9 0.086(2) 0.0455(18) 0.060(2) -0.0108(16) 0.0019(17) -0.0200(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.365(3) . ? O1 C2 1.442(3) . ? O4 C4 1.226(3) . ? O3 C4 1.364(3) . ? O3 C2 1.431(3) . ? O6 C6 1.219(3) . ? C4 C5 1.425(4) . ? N1 C7 1.323(3) . ? N1 C8 1.444(4) . ? N2 C7 1.336(3) . ? N2 C9 1.450(4) . ? C6 C5 1.427(4) . ? C5 C7 1.444(4) . ? C2 C22 1.498(4) . ? C2 C21 1.502(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 C2 118.1(2) . . ? C4 O3 C2 117.6(2) . . ? O4 C4 O3 115.9(2) . . ? O4 C4 C5 127.0(3) . . ? O3 C4 C5 116.8(2) . . ? C7 N1 C8 124.8(3) . . ? C7 N2 C9 126.2(3) . . ? O6 C6 O1 116.0(2) . . ? O6 C6 C5 127.2(3) . . ? O1 C6 C5 116.7(2) . . ? C4 C5 C6 118.9(2) . . ? C4 C5 C7 119.6(2) . . ? C6 C5 C7 120.2(2) . . ? O3 C2 O1 108.3(2) . . ? O3 C2 C22 106.7(2) . . ? O1 C2 C22 106.4(2) . . ? O3 C2 C21 111.2(2) . . ? O1 C2 C21 111.1(2) . . ? C22 C2 C21 112.9(3) . . ? N1 C7 N2 117.8(3) . . ? N1 C7 C5 120.6(2) . . ? N2 C7 C5 121.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O3 C4 O4 -164.1(2) . . . . ? C2 O3 C4 C5 20.5(3) . . . . ? C2 O1 C6 O6 165.6(2) . . . . ? C2 O1 C6 C5 -16.3(4) . . . . ? O4 C4 C5 C6 -159.3(3) . . . . ? O3 C4 C5 C6 15.5(4) . . . . ? O4 C4 C5 C7 7.9(4) . . . . ? O3 C4 C5 C7 -177.4(2) . . . . ? O6 C6 C5 C4 160.4(3) . . . . ? O1 C6 C5 C4 -17.5(4) . . . . ? O6 C6 C5 C7 -6.6(4) . . . . ? O1 C6 C5 C7 175.5(2) . . . . ? C4 O3 C2 O1 -51.2(3) . . . . ? C4 O3 C2 C22 -165.4(2) . . . . ? C4 O3 C2 C21 71.1(3) . . . . ? C6 O1 C2 O3 49.0(3) . . . . ? C6 O1 C2 C22 163.4(3) . . . . ? C6 O1 C2 C21 -73.4(3) . . . . ? C8 N1 C7 N2 6.7(4) . . . . ? C8 N1 C7 C5 -171.9(3) . . . . ? C9 N2 C7 N1 -165.6(3) . . . . ? C9 N2 C7 C5 12.9(4) . . . . ? C4 C5 C7 N1 -135.5(3) . . . . ? C6 C5 C7 N1 31.5(4) . . . . ? C4 C5 C7 N2 46.0(4) . . . . ? C6 C5 C7 N2 -147.1(3) . . . . ? #===END # Compound (11) # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-08-06 at 14:18:07 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 1738cw5 dreduc struct psi_scan data_1738cw5 _database_code_CSD 177776 _audit_creation_date 2001-08-06T14:18:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H13 N1 O4 S1' _chemical_formula_structural 'C9 H13 N O4 S' _chemical_formula_sum 'C9 H13 N O4 S' _chemical_formula_weight 231.26 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.9086(6) _cell_length_b 18.3810(10) _cell_length_c 10.4600(10) _cell_angle_alpha 90 _cell_angle_beta 104.460(10) _cell_angle_gamma 90 _cell_volume 1100.03(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_factor_muR 0.144 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.846 _exptl_absorpt_correction_T_max 0.8692 _exptl_absorpt_correction_T_ave 0.849 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.61416E-1 _diffrn_orient_matrix_ub_12 -0.35039E-1 _diffrn_orient_matrix_ub_13 -0.73574E-1 _diffrn_orient_matrix_ub_21 0.163119 _diffrn_orient_matrix_ub_22 -0.9939E-2 _diffrn_orient_matrix_ub_23 -0.6542E-2 _diffrn_orient_matrix_ub_31 0.13159E-1 _diffrn_orient_matrix_ub_32 -0.40408E-1 _diffrn_orient_matrix_ub_33 0.65482E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -3 _diffrn_standards_decay_corr_max 1.091 _diffrn_standards_decay_corr_min 0.965 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 6 4 3 -6 -2 1 -8 4 _diffrn_reflns_number 2119 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_unetI/netI 0.017 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1925 _reflns_number_gt 1502 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0537P)^2^+0.3438P] 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_number_reflns 1925 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.32 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 C2 C 0.6344(4) 0.11681(11) 0.1004(2) 0.0448(5) Uani 1 1 d . . . C4 C 0.6270(4) 0.06596(11) 0.3114(2) 0.0464(5) Uani 1 1 d . . . C5 C 0.7563(3) 0.12903(10) 0.36767(19) 0.0407(4) Uani 1 1 d . . . C6 C 0.7290(4) 0.19477(11) 0.2893(2) 0.0435(5) Uani 1 1 d . . . C7 C 0.8650(4) 0.13016(10) 0.5055(2) 0.0432(5) Uani 1 1 d . . . C8 C 0.9056(5) 0.07855(13) 0.7279(2) 0.0634(7) Uani 1 1 d . . . H8A H 0.8171 0.0447 0.7658 0.095 Uiso 1 1 calc R . . H8B H 0.911 0.1247 0.7715 0.095 Uiso 1 1 calc R . . H8C H 1.0617 0.0605 0.7386 0.095 Uiso 1 1 calc R . . C9 C 1.2549(5) 0.19460(17) 0.4507(3) 0.0747(8) Uani 1 1 d . . . H9A H 1.3902 0.2248 0.4815 0.112 Uiso 1 1 calc R . . H9B H 1.1534 0.2164 0.3741 0.112 Uiso 1 1 calc R . . H9C H 1.3026 0.1474 0.4282 0.112 Uiso 1 1 calc R . . C21 C 0.8789(4) 0.09893(13) 0.0929(2) 0.0556(6) Uani 1 1 d . . . H21A H 0.8805 0.0519 0.0531 0.083 Uiso 1 1 calc R . . H21B H 0.9805 0.0985 0.1803 0.083 Uiso 1 1 calc R . . H21C H 0.9318 0.1349 0.0405 0.083 Uiso 1 1 calc R . . C22 C 0.4637(5) 0.11750(14) -0.0326(2) 0.0618(6) Uani 1 1 d . . . H22A H 0.4649 0.071 -0.0742 0.093 Uiso 1 1 calc R . . H22B H 0.5073 0.1546 -0.0864 0.093 Uiso 1 1 calc R . . H22C H 0.3097 0.1273 -0.0222 0.093 Uiso 1 1 calc R . . N1 N 0.7952(3) 0.08732(10) 0.58808(17) 0.0492(4) Uani 1 1 d . . . H1 H 0.674(5) 0.0589(15) 0.551(3) 0.069(8) Uiso 1 1 d . . . O1 O 0.6255(3) 0.18671(7) 0.15809(14) 0.0476(4) Uani 1 1 d . . . O3 O 0.5476(3) 0.06347(8) 0.17796(13) 0.0524(4) Uani 1 1 d . . . O4 O 0.5770(3) 0.01393(9) 0.37170(15) 0.0676(5) Uani 1 1 d . . . O6 O 0.7729(3) 0.25640(8) 0.32916(16) 0.0602(4) Uani 1 1 d . . . S2 S 1.10285(11) 0.18581(3) 0.57772(6) 0.0592(2) 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 C2 0.0535(12) 0.0409(11) 0.0439(11) 0.0005(8) 0.0195(9) -0.0046(9) C4 0.0552(13) 0.0468(11) 0.0422(11) -0.0031(9) 0.0216(10) -0.0113(9) C5 0.0425(11) 0.0386(10) 0.0432(10) -0.0011(8) 0.0151(8) -0.0043(8) C6 0.0442(11) 0.0398(11) 0.0503(12) -0.0016(9) 0.0192(9) 0.0009(9) C7 0.0448(11) 0.0375(10) 0.0493(12) -0.0037(9) 0.0153(9) 0.0002(8) C8 0.0857(18) 0.0554(14) 0.0434(12) 0.0066(10) 0.0053(12) -0.0026(13) C9 0.0510(14) 0.089(2) 0.089(2) -0.0233(15) 0.0273(13) -0.0195(13) C21 0.0632(14) 0.0541(13) 0.0563(13) 0.0022(10) 0.0279(11) 0.0034(11) C22 0.0681(16) 0.0704(16) 0.0461(13) 0.0009(11) 0.0127(11) -0.0052(12) N1 0.0574(11) 0.0473(10) 0.0409(9) 0.0026(8) 0.0082(8) -0.0068(9) O1 0.0553(9) 0.0416(8) 0.0464(8) 0.0021(6) 0.0135(7) 0.0046(6) O3 0.0669(10) 0.0512(9) 0.0420(8) -0.0036(6) 0.0189(7) -0.0213(7) O4 0.1001(14) 0.0586(10) 0.0484(9) -0.0025(7) 0.0265(9) -0.0380(9) O6 0.0846(12) 0.0345(8) 0.0633(10) -0.0039(7) 0.0219(9) 0.0006(7) S2 0.0573(4) 0.0609(4) 0.0573(4) -0.0121(3) 0.0107(3) -0.0153(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 O1 1.426(2) . ? C2 O3 1.446(2) . ? C2 C22 1.500(3) . ? C2 C21 1.503(3) . ? C4 O4 1.222(2) . ? C4 O3 1.358(2) . ? C4 C5 1.432(3) . ? C5 C7 1.425(3) . ? C5 C6 1.446(3) . ? C6 O6 1.213(2) . ? C6 O1 1.364(3) . ? C7 N1 1.309(3) . ? C7 S2 1.750(2) . ? C8 N1 1.454(3) . ? C9 S2 1.787(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 O1 C2 O3 108.54(15) . . ? O1 C2 C22 107.31(18) . . ? O3 C2 C22 105.99(17) . . ? O1 C2 C21 110.89(18) . . ? O3 C2 C21 111.17(17) . . ? C22 C2 C21 112.70(19) . . ? O4 C4 O3 116.01(18) . . ? O4 C4 C5 126.47(19) . . ? O3 C4 C5 117.51(17) . . ? C7 C5 C4 119.16(18) . . ? C7 C5 C6 121.32(18) . . ? C4 C5 C6 118.10(18) . . ? O6 C6 O1 116.82(18) . . ? O6 C6 C5 127.0(2) . . ? O1 C6 C5 115.98(17) . . ? N1 C7 C5 121.49(19) . . ? N1 C7 S2 114.73(16) . . ? C5 C7 S2 123.76(15) . . ? C7 N1 C8 126.5(2) . . ? C6 O1 C2 117.97(15) . . ? C4 O3 C2 118.31(15) . . ? C7 S2 C9 103.34(11) . . ? 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 O4 C4 C5 C7 8.2(3) . . . . ? O3 C4 C5 C7 -172.95(18) . . . . ? O4 C4 C5 C6 -158.4(2) . . . . ? O3 C4 C5 C6 20.5(3) . . . . ? C7 C5 C6 O6 -6.6(3) . . . . ? C4 C5 C6 O6 159.7(2) . . . . ? C7 C5 C6 O1 179.05(17) . . . . ? C4 C5 C6 O1 -14.7(3) . . . . ? C4 C5 C7 N1 -21.2(3) . . . . ? C6 C5 C7 N1 144.9(2) . . . . ? C4 C5 C7 S2 157.07(16) . . . . ? C6 C5 C7 S2 -36.8(3) . . . . ? C5 C7 N1 C8 173.7(2) . . . . ? S2 C7 N1 C8 -4.8(3) . . . . ? O6 C6 O1 C2 161.70(18) . . . . ? C5 C6 O1 C2 -23.3(2) . . . . ? O3 C2 O1 C6 52.7(2) . . . . ? C22 C2 O1 C6 166.83(17) . . . . ? C21 C2 O1 C6 -69.7(2) . . . . ? O4 C4 O3 C2 -169.48(19) . . . . ? C5 C4 O3 C2 11.6(3) . . . . ? O1 C2 O3 C4 -46.3(2) . . . . ? C22 C2 O3 C4 -161.32(19) . . . . ? C21 C2 O3 C4 75.9(2) . . . . ? N1 C7 S2 C9 147.80(18) . . . . ? C5 C7 S2 C9 -30.6(2) . . . . ? #===END # Compound (12) # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-10-16 at 10:32:21 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 1005dm4 data_1005dm4 _database_code_CSD 177777 _audit_creation_date 2001-10-16T10:32:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C14 H15 N O4 S' _chemical_formula_weight 293.33 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 13.850(4) _cell_length_b 5.4148(5) _cell_length_c 18.675(7) _cell_angle_alpha 90 _cell_angle_beta 91.85(2) _cell_angle_gamma 90 _cell_volume 1399.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_T_min 0.8677 _exptl_absorpt_correction_T_max 0.9529 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 2570 _diffrn_reflns_av_R_equivalents 0.0098 _diffrn_reflns_av_unetI/netI 0.0147 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2461 _reflns_number_gt 1983 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0560P)^2^+0.5263P] 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_number_reflns 2461 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.049 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.248 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 C2 C 0.03501(14) 0.0999(4) 0.38691(11) 0.0460(5) Uani 1 1 d . . . C4 C 0.16705(13) 0.2746(3) 0.45577(10) 0.0413(4) Uani 1 1 d . . . C5 C 0.22060(13) 0.2598(3) 0.39100(9) 0.0391(4) Uani 1 1 d . . . C6 C 0.16789(14) 0.2657(4) 0.32295(10) 0.0424(4) Uani 1 1 d . . . C7 C 0.32235(13) 0.2718(3) 0.39235(9) 0.0394(4) Uani 1 1 d . . . C9 C 0.32925(17) -0.0950(5) 0.49906(14) 0.0689(7) Uani 1 1 d . . . H9A H 0.3667 -0.1705 0.5373 0.103 Uiso 1 1 calc R . . H9B H 0.3139 -0.2163 0.4629 0.103 Uiso 1 1 calc R . . H9C H 0.2706 -0.0297 0.5175 0.103 Uiso 1 1 calc R . . C11 C 0.47211(14) 0.3612(4) 0.33080(10) 0.0420(4) Uani 1 1 d . . . C12 C 0.53072(16) 0.5434(4) 0.35903(12) 0.0593(6) Uani 1 1 d . . . H12 H 0.5045 0.676 0.3834 0.071 Uiso 1 1 calc R . . C13 C 0.62928(18) 0.5270(6) 0.35079(15) 0.0749(8) Uani 1 1 d . . . H13 H 0.6699 0.6478 0.3704 0.09 Uiso 1 1 calc R . . C14 C 0.66731(17) 0.3348(6) 0.31404(15) 0.0745(8) Uani 1 1 d . . . H14 H 0.7336 0.3255 0.3081 0.089 Uiso 1 1 calc R . . C15 C 0.60774(19) 0.1553(6) 0.28583(14) 0.0735(7) Uani 1 1 d . . . H15 H 0.6339 0.0244 0.2607 0.088 Uiso 1 1 calc R . . C16 C 0.50997(16) 0.1669(4) 0.29440(11) 0.0573(6) Uani 1 1 d . . . H16 H 0.4698 0.0438 0.2756 0.069 Uiso 1 1 calc R . . C21 C 0.06306(18) -0.1692(4) 0.39082(13) 0.0595(6) Uani 1 1 d . . . H21A H 0.0387 -0.2529 0.3487 0.089 Uiso 1 1 calc R . . H21B H 0.0362 -0.2426 0.4325 0.089 Uiso 1 1 calc R . . H21C H 0.1322 -0.1831 0.3937 0.089 Uiso 1 1 calc R . . C22 C -0.07262(16) 0.1392(5) 0.38320(14) 0.0660(6) Uani 1 1 d . . . H22A H -0.0999 0.0552 0.342 0.099 Uiso 1 1 calc R . . H22B H -0.0862 0.3126 0.3794 0.099 Uiso 1 1 calc R . . H22C H -0.1004 0.0749 0.4258 0.099 Uiso 1 1 calc R . . N1 N 0.36971(12) 0.3742(3) 0.33939(9) 0.0493(4) Uani 1 1 d . . . O1 O 0.07228(9) 0.2145(3) 0.32402(7) 0.0479(3) Uani 1 1 d . . . O3 O 0.07056(9) 0.2299(2) 0.44909(7) 0.0453(3) Uani 1 1 d . . . O4 O 0.19790(10) 0.3371(3) 0.51456(7) 0.0572(4) Uani 1 1 d . . . O6 O 0.20024(10) 0.3159(3) 0.26474(7) 0.0559(4) Uani 1 1 d . . . S2 S 0.39767(4) 0.15075(11) 0.46063(3) 0.0528(2) Uani 1 1 d . . . H1 H 0.3326(18) 0.439(5) 0.3046(14) 0.072(7) Uiso 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 C2 0.0443(10) 0.0392(10) 0.0539(11) 0.0031(9) -0.0072(9) -0.0026(8) C4 0.0386(10) 0.0352(10) 0.0498(11) -0.0012(8) -0.0034(8) 0.0027(8) C5 0.0377(9) 0.0377(10) 0.0414(9) 0.0005(8) -0.0065(7) 0.0037(8) C6 0.0413(10) 0.0358(10) 0.0494(11) 0.0009(9) -0.0088(8) 0.0065(8) C7 0.0397(10) 0.0384(10) 0.0397(9) 0.0012(8) -0.0042(8) 0.0046(8) C9 0.0550(13) 0.0722(17) 0.0792(16) 0.0349(13) -0.0003(12) 0.0089(12) C11 0.0391(9) 0.0509(11) 0.0357(9) 0.0082(8) -0.0034(7) -0.0003(8) C12 0.0577(13) 0.0554(13) 0.0643(14) -0.0051(11) -0.0051(10) -0.0044(11) C13 0.0540(14) 0.0840(19) 0.0854(18) 0.0125(16) -0.0164(13) -0.0243(14) C14 0.0400(12) 0.108(2) 0.0756(16) 0.0346(17) 0.0064(11) 0.0028(14) C15 0.0638(15) 0.0873(19) 0.0704(16) 0.0009(14) 0.0180(13) 0.0160(14) C16 0.0585(13) 0.0601(14) 0.0531(12) -0.0066(11) 0.0015(10) -0.0039(11) C21 0.0689(15) 0.0383(11) 0.0703(14) -0.0008(10) -0.0121(11) -0.0031(10) C22 0.0417(11) 0.0702(16) 0.0853(17) 0.0100(13) -0.0106(11) -0.0064(11) N1 0.0380(9) 0.0639(12) 0.0456(9) 0.0154(9) -0.0055(7) 0.0033(8) O1 0.0403(7) 0.0491(8) 0.0533(8) 0.0074(7) -0.0135(6) -0.0019(6) O3 0.0366(7) 0.0435(8) 0.0558(8) -0.0051(6) -0.0009(6) 0.0016(6) O4 0.0494(8) 0.0740(10) 0.0478(8) -0.0136(7) -0.0027(6) -0.0030(7) O6 0.0507(8) 0.0716(10) 0.0447(8) 0.0107(7) -0.0088(6) -0.0003(7) S2 0.0378(3) 0.0700(4) 0.0501(3) 0.0187(3) -0.0078(2) 0.0028(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 O3 1.431(2) . ? C2 O1 1.439(2) . ? C2 C22 1.505(3) . ? C2 C21 1.509(3) . ? C4 O4 1.213(2) . ? C4 O3 1.360(2) . ? C4 C5 1.441(3) . ? C5 C7 1.410(2) . ? C5 C6 1.445(3) . ? C6 O6 1.220(2) . ? C6 O1 1.354(2) . ? C7 N1 1.326(2) . ? C7 S2 1.7488(19) . ? C9 S2 1.797(2) . ? C11 C16 1.366(3) . ? C11 C12 1.372(3) . ? C11 N1 1.434(2) . ? C12 C13 1.381(3) . ? C13 C14 1.362(4) . ? C14 C15 1.369(4) . ? C15 C16 1.370(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 O3 C2 O1 109.09(15) . . ? O3 C2 C22 106.38(17) . . ? O1 C2 C22 106.40(16) . . ? O3 C2 C21 110.74(17) . . ? O1 C2 C21 110.94(18) . . ? C22 C2 C21 113.06(18) . . ? O4 C4 O3 116.68(17) . . ? O4 C4 C5 126.82(18) . . ? O3 C4 C5 116.35(16) . . ? C7 C5 C4 121.56(16) . . ? C7 C5 C6 119.39(17) . . ? C4 C5 C6 118.53(16) . . ? O6 C6 O1 116.51(17) . . ? O6 C6 C5 126.79(18) . . ? O1 C6 C5 116.68(17) . . ? N1 C7 C5 121.62(16) . . ? N1 C7 S2 113.75(14) . . ? C5 C7 S2 124.60(14) . . ? C16 C11 C12 120.9(2) . . ? C16 C11 N1 119.36(18) . . ? C12 C11 N1 119.77(19) . . ? C11 C12 C13 119.0(2) . . ? C14 C13 C12 120.3(2) . . ? C13 C14 C15 119.9(2) . . ? C14 C15 C16 120.5(3) . . ? C11 C16 C15 119.4(2) . . ? C7 N1 C11 125.29(16) . . ? C6 O1 C2 118.50(14) . . ? C4 O3 C2 118.24(15) . . ? C7 S2 C9 105.02(10) . . ? 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 O4 C4 C5 C7 12.8(3) . . . . ? O3 C4 C5 C7 -172.00(17) . . . . ? O4 C4 C5 C6 -158.9(2) . . . . ? O3 C4 C5 C6 16.3(3) . . . . ? C7 C5 C6 O6 -11.4(3) . . . . ? C4 C5 C6 O6 160.5(2) . . . . ? C7 C5 C6 O1 169.88(17) . . . . ? C4 C5 C6 O1 -18.2(3) . . . . ? C4 C5 C7 N1 -147.02(19) . . . . ? C6 C5 C7 N1 24.6(3) . . . . ? C4 C5 C7 S2 34.6(3) . . . . ? C6 C5 C7 S2 -153.74(15) . . . . ? C16 C11 C12 C13 -0.6(3) . . . . ? N1 C11 C12 C13 179.5(2) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? C12 C13 C14 C15 -0.8(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? N1 C11 C16 C15 179.6(2) . . . . ? C14 C15 C16 C11 0.7(4) . . . . ? C5 C7 N1 C11 -169.82(19) . . . . ? S2 C7 N1 C11 8.7(3) . . . . ? C16 C11 N1 C7 87.8(3) . . . . ? C12 C11 N1 C7 -92.3(3) . . . . ? O6 C6 O1 C2 165.81(17) . . . . ? C5 C6 O1 C2 -15.3(2) . . . . ? O3 C2 O1 C6 48.0(2) . . . . ? C22 C2 O1 C6 162.40(18) . . . . ? C21 C2 O1 C6 -74.2(2) . . . . ? O4 C4 O3 C2 -165.04(17) . . . . ? C5 C4 O3 C2 19.2(2) . . . . ? O1 C2 O3 C4 -50.1(2) . . . . ? C22 C2 O3 C4 -164.50(17) . . . . ? C21 C2 O3 C4 72.3(2) . . . . ? N1 C7 S2 C9 -152.39(16) . . . . ? C5 C7 S2 C9 26.1(2) . . . . ? #===END # Compound (13) # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-08-06 at 13:06:33 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : cw10187 dreduc struct psi_scan data_cw10187 _database_code_CSD 177778 _audit_creation_date 2001-08-06T13:06:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H23 N1 O4 S1' _chemical_formula_structural 'C18 H23 N O4 S' _chemical_formula_sum 'C18 H23 N O4 S' _chemical_formula_weight 349.43 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8985(9) _cell_length_b 8.4510(10) _cell_length_c 19.677(2) _cell_angle_alpha 90 _cell_angle_beta 97.630(10) _cell_angle_gamma 90 _cell_volume 1796.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_factor_muR 0.101 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.8889 _exptl_absorpt_correction_T_max 0.9061 _exptl_absorpt_correction_T_ave 0.817 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.6409E-2 _diffrn_orient_matrix_ub_12 0.14333E-1 _diffrn_orient_matrix_ub_13 0.49838E-1 _diffrn_orient_matrix_ub_21 0.3163E-2 _diffrn_orient_matrix_ub_22 -0.117307 _diffrn_orient_matrix_ub_23 0.6555E-2 _diffrn_orient_matrix_ub_31 0.92326E-1 _diffrn_orient_matrix_ub_32 0.5011E-2 _diffrn_orient_matrix_ub_33 0.01 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -3 _diffrn_standards_decay_corr_max 1.05 _diffrn_standards_decay_corr_min 0.87 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -1 11 6 -2 -2 6 1 -5 _diffrn_reflns_number 3313 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_unetI/netI 0.0396 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 3135 _reflns_number_gt 2025 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0976P)^2^+0.2451P] 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_number_reflns 3135 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1366 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.494 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.062 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 C2 C 0.6167(3) 0.3404(4) 0.93817(13) 0.0438(7) Uani 1 1 d . . . C4 C 0.4377(3) 0.4294(3) 0.86338(13) 0.0359(6) Uani 1 1 d . . . C5 C 0.4498(2) 0.2850(3) 0.82548(13) 0.0350(6) Uani 1 1 d . . . C6 C 0.5698(3) 0.2128(3) 0.82866(13) 0.0349(6) Uani 1 1 d . . . C7 C 0.3479(3) 0.2319(3) 0.77895(14) 0.0371(6) Uani 1 1 d . . . C8 C 0.3965(4) -0.0795(4) 0.82433(18) 0.0595(9) Uani 1 1 d . . . H8A H 0.3845 -0.1901 0.8143 0.089 Uiso 1 1 calc R . . H8B H 0.3628 -0.0543 0.8657 0.089 Uiso 1 1 calc R . . H8C H 0.4834 -0.0557 0.8302 0.089 Uiso 1 1 calc R . . C9 C 0.1430(3) 0.2923(4) 0.71515(16) 0.0455(7) Uani 1 1 d . . . C10 C 0.0477(3) 0.2530(4) 0.75320(17) 0.0540(8) Uani 1 1 d . . . C11 C -0.0665(3) 0.2190(5) 0.7170(2) 0.0662(10) Uani 1 1 d . . . H11 H -0.1316 0.1915 0.7408 0.079 Uiso 1 1 calc R . . C12 C -0.0862(3) 0.2248(5) 0.6467(2) 0.0724(11) Uani 1 1 d . . . H12 H -0.1641 0.2018 0.6234 0.087 Uiso 1 1 calc R . . C13 C 0.0087(3) 0.2645(5) 0.61111(19) 0.0664(10) Uani 1 1 d . . . H13 H -0.0058 0.2676 0.5635 0.08 Uiso 1 1 calc R . . C14 C 0.1252(3) 0.3001(4) 0.64356(16) 0.0489(8) Uani 1 1 d . . . C15 C 0.0706(4) 0.2456(6) 0.8305(2) 0.0781(12) Uani 1 1 d . . . H15A H 0.1001 0.1402 0.8436 0.094 Uiso 1 1 calc R . . H15B H 0.1366 0.3191 0.8462 0.094 Uiso 1 1 calc R . . C16 C -0.0322(4) 0.2800(9) 0.8660(2) 0.119(2) Uani 1 1 d . . . H16A H -0.007 0.2721 0.9145 0.179 Uiso 1 1 calc R . . H16B H -0.0976 0.2058 0.8525 0.179 Uiso 1 1 calc R . . H16C H -0.0612 0.3853 0.8549 0.179 Uiso 1 1 calc R . . C17 C 0.2330(3) 0.3437(5) 0.60562(17) 0.0623(10) Uani 1 1 d . . . H17A H 0.2714 0.4387 0.6263 0.075 Uiso 1 1 calc R . . H17B H 0.2939 0.2595 0.6125 0.075 Uiso 1 1 calc R . . C18 C 0.2016(4) 0.3720(6) 0.5294(2) 0.0859(13) Uani 1 1 d . . . H18A H 0.2757 0.3984 0.5104 0.129 Uiso 1 1 calc R . . H18B H 0.1436 0.4576 0.5217 0.129 Uiso 1 1 calc R . . H18C H 0.1658 0.2779 0.5078 0.129 Uiso 1 1 calc R . . C21 C 0.5546(4) 0.2303(4) 0.98311(16) 0.0608(9) Uani 1 1 d . . . H21A H 0.5291 0.2886 1.0207 0.091 Uiso 1 1 calc R . . H21B H 0.6115 0.1487 1.0005 0.091 Uiso 1 1 calc R . . H21C H 0.4834 0.1832 0.9568 0.091 Uiso 1 1 calc R . . C22 C 0.7308(3) 0.4180(5) 0.97472(18) 0.0663(10) Uani 1 1 d . . . H22A H 0.7097 0.4758 1.0136 0.099 Uiso 1 1 calc R . . H22B H 0.7644 0.4893 0.944 0.099 Uiso 1 1 calc R . . H22C H 0.7911 0.3385 0.99 0.099 Uiso 1 1 calc R . . N1 N 0.2627(2) 0.3322(3) 0.75109(13) 0.0453(6) Uani 1 1 d . . . O1 O 0.65658(17) 0.2566(2) 0.88133(9) 0.0435(5) Uani 1 1 d . . . O3 O 0.53496(18) 0.4648(2) 0.91271(9) 0.0425(5) Uani 1 1 d . . . O4 O 0.35294(19) 0.5224(2) 0.85659(10) 0.0441(5) Uani 1 1 d . . . O6 O 0.60347(18) 0.1227(3) 0.78694(9) 0.0461(5) Uani 1 1 d . . . S1 S 0.31967(8) 0.03483(10) 0.75511(4) 0.0504(3) Uani 1 1 d . . . H1 H 0.279(3) 0.440(5) 0.7579(18) 0.070(12) Uiso 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 C2 0.0492(17) 0.0498(18) 0.0320(14) -0.0038(13) 0.0034(13) 0.0124(14) C4 0.0366(15) 0.0406(16) 0.0307(14) 0.0018(11) 0.0050(11) 0.0015(13) C5 0.0348(15) 0.0391(15) 0.0311(13) -0.0011(11) 0.0050(11) 0.0004(12) C6 0.0361(15) 0.0383(15) 0.0304(13) 0.0014(12) 0.0044(11) 0.0032(12) C7 0.0360(15) 0.0417(16) 0.0349(14) -0.0008(12) 0.0098(12) 0.0020(13) C8 0.078(2) 0.0393(18) 0.060(2) 0.0057(15) 0.0063(18) -0.0015(17) C9 0.0366(16) 0.0449(17) 0.0520(17) -0.0044(14) -0.0048(14) -0.0011(14) C10 0.0444(18) 0.064(2) 0.0525(19) -0.0006(16) 0.0020(15) 0.0021(16) C11 0.0400(19) 0.087(3) 0.072(2) 0.002(2) 0.0088(17) -0.0109(19) C12 0.044(2) 0.103(3) 0.066(2) -0.002(2) -0.0093(17) -0.014(2) C13 0.053(2) 0.087(3) 0.056(2) -0.0050(19) -0.0074(17) -0.0146(19) C14 0.0411(17) 0.0560(19) 0.0479(17) -0.0046(15) -0.0005(14) -0.0047(15) C15 0.059(2) 0.118(4) 0.058(2) 0.006(2) 0.0101(18) 0.003(2) C16 0.081(3) 0.207(7) 0.073(3) 0.011(4) 0.019(3) 0.021(4) C17 0.054(2) 0.074(2) 0.059(2) -0.0072(18) 0.0050(16) -0.0156(18) C18 0.077(3) 0.113(4) 0.067(2) 0.015(3) 0.008(2) -0.019(3) C21 0.086(3) 0.059(2) 0.0403(17) 0.0046(15) 0.0161(17) 0.0137(19) C22 0.055(2) 0.087(3) 0.0516(19) -0.0185(19) -0.0109(16) 0.0074(19) N1 0.0371(14) 0.0424(16) 0.0531(15) -0.0003(12) -0.0057(11) 0.0000(12) O1 0.0350(11) 0.0585(13) 0.0355(10) -0.0073(9) -0.0003(8) 0.0101(9) O3 0.0449(11) 0.0436(11) 0.0365(10) -0.0079(9) -0.0033(8) 0.0049(9) O4 0.0441(12) 0.0444(11) 0.0431(11) -0.0049(9) 0.0033(9) 0.0132(10) O6 0.0482(12) 0.0517(13) 0.0388(11) -0.0089(10) 0.0072(9) 0.0147(10) S1 0.0549(5) 0.0401(4) 0.0535(5) -0.0079(4) -0.0031(4) -0.0020(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 O3 1.425(3) . ? C2 O1 1.439(3) . ? C2 C22 1.502(5) . ? C2 C21 1.506(5) . ? C4 O4 1.207(3) . ? C4 O3 1.372(3) . ? C4 C5 1.445(4) . ? C5 C7 1.416(4) . ? C5 C6 1.437(4) . ? C6 O6 1.212(3) . ? C6 O1 1.358(3) . ? C7 N1 1.321(4) . ? C7 S1 1.747(3) . ? C8 S1 1.785(3) . ? C9 C14 1.398(4) . ? C9 C10 1.398(5) . ? C9 N1 1.438(4) . ? C10 C11 1.380(5) . ? C10 C15 1.509(5) . ? C11 C12 1.371(5) . ? C12 C13 1.366(6) . ? C13 C14 1.377(4) . ? C14 C17 1.518(5) . ? C15 C16 1.427(6) . ? C17 C18 1.511(5) . ? 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 O3 C2 O1 109.2(2) . . ? O3 C2 C22 106.6(3) . . ? O1 C2 C22 105.7(3) . . ? O3 C2 C21 110.7(3) . . ? O1 C2 C21 111.0(3) . . ? C22 C2 C21 113.4(3) . . ? O4 C4 O3 116.4(2) . . ? O4 C4 C5 127.9(2) . . ? O3 C4 C5 115.7(2) . . ? C7 C5 C6 121.7(3) . . ? C7 C5 C4 118.9(2) . . ? C6 C5 C4 118.7(2) . . ? O6 C6 O1 116.5(2) . . ? O6 C6 C5 126.4(2) . . ? O1 C6 C5 117.1(2) . . ? N1 C7 C5 120.9(3) . . ? N1 C7 S1 114.3(2) . . ? C5 C7 S1 124.8(2) . . ? C14 C9 C10 122.5(3) . . ? C14 C9 N1 118.7(3) . . ? C10 C9 N1 118.8(3) . . ? C11 C10 C9 117.1(3) . . ? C11 C10 C15 121.9(3) . . ? C9 C10 C15 121.0(3) . . ? C12 C11 C10 121.5(3) . . ? C13 C12 C11 119.8(3) . . ? C12 C13 C14 122.0(3) . . ? C13 C14 C9 116.9(3) . . ? C13 C14 C17 123.4(3) . . ? C9 C14 C17 119.6(3) . . ? C16 C15 C10 116.7(4) . . ? C18 C17 C14 116.0(3) . . ? C7 N1 C9 126.5(3) . . ? C6 O1 C2 118.4(2) . . ? C4 O3 C2 118.5(2) . . ? C7 S1 C8 105.27(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 O4 C4 C5 C7 -7.1(4) . . . . ? O3 C4 C5 C7 173.3(2) . . . . ? O4 C4 C5 C6 163.9(3) . . . . ? O3 C4 C5 C6 -15.7(4) . . . . ? C7 C5 C6 O6 13.3(5) . . . . ? C4 C5 C6 O6 -157.4(3) . . . . ? C7 C5 C6 O1 -170.8(3) . . . . ? C4 C5 C6 O1 18.5(4) . . . . ? C6 C5 C7 N1 -146.1(3) . . . . ? C4 C5 C7 N1 24.6(4) . . . . ? C6 C5 C7 S1 35.8(4) . . . . ? C4 C5 C7 S1 -153.5(2) . . . . ? C14 C9 C10 C11 1.0(5) . . . . ? N1 C9 C10 C11 178.5(3) . . . . ? C14 C9 C10 C15 179.9(3) . . . . ? N1 C9 C10 C15 -2.6(5) . . . . ? C9 C10 C11 C12 -0.6(6) . . . . ? C15 C10 C11 C12 -179.5(4) . . . . ? C10 C11 C12 C13 0.2(7) . . . . ? C11 C12 C13 C14 -0.3(7) . . . . ? C12 C13 C14 C9 0.6(6) . . . . ? C12 C13 C14 C17 179.6(4) . . . . ? C10 C9 C14 C13 -1.0(5) . . . . ? N1 C9 C14 C13 -178.5(3) . . . . ? C10 C9 C14 C17 180.0(3) . . . . ? N1 C9 C14 C17 2.4(5) . . . . ? C11 C10 C15 C16 -30.2(7) . . . . ? C9 C10 C15 C16 150.9(5) . . . . ? C13 C14 C17 C18 9.4(6) . . . . ? C9 C14 C17 C18 -171.6(4) . . . . ? C5 C7 N1 C9 -166.0(3) . . . . ? S1 C7 N1 C9 12.2(4) . . . . ? C14 C9 N1 C7 -103.0(4) . . . . ? C10 C9 N1 C7 79.4(4) . . . . ? O6 C6 O1 C2 -169.3(2) . . . . ? C5 C6 O1 C2 14.4(4) . . . . ? O3 C2 O1 C6 -47.3(3) . . . . ? C22 C2 O1 C6 -161.6(3) . . . . ? C21 C2 O1 C6 75.0(3) . . . . ? O4 C4 O3 C2 160.2(2) . . . . ? C5 C4 O3 C2 -20.1(3) . . . . ? O1 C2 O3 C4 50.4(3) . . . . ? C22 C2 O3 C4 164.2(2) . . . . ? C21 C2 O3 C4 -72.1(3) . . . . ? N1 C7 S1 C8 -153.6(2) . . . . ? C5 C7 S1 C8 24.5(3) . . . . ? #===END # Compound (14) # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-10-16 at 10:36:14 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 989dm3 data_989dm3 _database_code_CSD 177779 _audit_creation_date 2001-10-16T10:36:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C14 H15 N O5' _chemical_formula_weight 277.27 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2148(6) _cell_length_b 9.5460(6) _cell_length_c 12.0590(10) _cell_angle_alpha 96.940(6) _cell_angle_beta 99.553(8) _cell_angle_gamma 105.438(7) _cell_volume 669.72(10) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9864 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 2543 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_unetI/netI 0.0495 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 2317 _reflns_number_gt 1361 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0804P)^2^+0.0976P] 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_number_reflns 2317 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.267 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C 0.1572(5) 0.4323(3) 0.6699(2) 0.0437(7) Uani 1 1 d . . . C4 C 0.0408(5) 0.3094(3) 0.8217(3) 0.0422(7) Uani 1 1 d . . . C5 C -0.1814(4) 0.2498(3) 0.7473(2) 0.0383(7) Uani 1 1 d . . . C6 C -0.1981(5) 0.2376(3) 0.6260(2) 0.0422(7) Uani 1 1 d . . . C7 C -0.3716(5) 0.1754(3) 0.7893(2) 0.0411(7) Uani 1 1 d . . . C10 C -0.3189(6) 0.3523(4) 0.9607(3) 0.0662(10) Uani 1 1 d . . . H10A H -0.3472 0.3508 1.0365 0.099 Uiso 1 1 calc R . . H10B H -0.4018 0.4108 0.9229 0.099 Uiso 1 1 calc R . . H10C H -0.1586 0.3942 0.9648 0.099 Uiso 1 1 calc R . . C11 C -0.7601(5) -0.0051(3) 0.7462(2) 0.0382(6) Uani 1 1 d . . . C12 C -0.9408(5) -0.0505(3) 0.6544(3) 0.0472(7) Uani 1 1 d . . . H12 H -0.9178 -0.0321 0.5826 0.057 Uiso 1 1 calc R . . C13 C -1.1571(5) -0.1235(3) 0.6678(3) 0.0569(9) Uani 1 1 d . . . H13 H -1.2795 -0.1528 0.6057 0.068 Uiso 1 1 calc R . . C14 C -1.1887(6) -0.1521(3) 0.7732(3) 0.0605(9) Uani 1 1 d . . . H14 H -1.3339 -0.1999 0.7829 0.073 Uiso 1 1 calc R . . C15 C -1.0090(6) -0.1111(3) 0.8645(3) 0.0619(9) Uani 1 1 d . . . H15 H -1.0318 -0.1328 0.9355 0.074 Uiso 1 1 calc R . . C16 C -0.7930(5) -0.0373(3) 0.8512(3) 0.0533(8) Uani 1 1 d . . . H16 H -0.6705 -0.0096 0.9133 0.064 Uiso 1 1 calc R . . C21 C 0.0746(6) 0.5653(3) 0.6932(3) 0.0582(9) Uani 1 1 d . . . H21A H 0.0374 0.5999 0.623 0.087 Uiso 1 1 calc R . . H21B H 0.1923 0.6419 0.7458 0.087 Uiso 1 1 calc R . . H21C H -0.0586 0.5389 0.7256 0.087 Uiso 1 1 calc R . . C22 C 0.3650(6) 0.4617(4) 0.6182(3) 0.0663(10) Uani 1 1 d . . . H22A H 0.3338 0.4987 0.5486 0.099 Uiso 1 1 calc R . . H22B H 0.4044 0.3718 0.6022 0.099 Uiso 1 1 calc R . . H22C H 0.4898 0.5335 0.6707 0.099 Uiso 1 1 calc R . . N1 N -0.5439(4) 0.0698(2) 0.7232(2) 0.0430(6) Uani 1 1 d . . . O1 O -0.0152(3) 0.3170(2) 0.58888(16) 0.0481(5) Uani 1 1 d . . . O2 O -0.3936(4) 0.2017(2) 0.89663(17) 0.0554(6) Uani 1 1 d . . . O3 O 0.2150(3) 0.3777(2) 0.77249(17) 0.0479(5) Uani 1 1 d . . . O4 O 0.0929(3) 0.2998(2) 0.92111(18) 0.0552(6) Uani 1 1 d . . . O6 O -0.3584(3) 0.1606(2) 0.55122(16) 0.0534(6) Uani 1 1 d . . . H1 H -0.535(6) 0.058(3) 0.646(3) 0.065(10) Uiso 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 C2 0.0369(16) 0.0444(16) 0.0458(17) 0.0078(13) 0.0091(13) 0.0048(13) C4 0.0404(16) 0.0384(15) 0.0498(19) 0.0114(13) 0.0125(14) 0.0114(13) C5 0.0336(15) 0.0381(14) 0.0388(15) 0.0042(12) 0.0063(12) 0.0050(12) C6 0.0387(16) 0.0400(15) 0.0460(18) 0.0033(13) 0.0103(14) 0.0091(13) C7 0.0405(16) 0.0403(15) 0.0407(16) 0.0057(13) 0.0064(13) 0.0105(13) C10 0.056(2) 0.073(2) 0.059(2) -0.0153(17) 0.0124(17) 0.0135(18) C11 0.0364(15) 0.0339(14) 0.0430(16) 0.0059(12) 0.0107(13) 0.0072(12) C12 0.0442(18) 0.0465(16) 0.0460(17) 0.0072(13) 0.0045(14) 0.0085(14) C13 0.0395(18) 0.0531(19) 0.068(2) 0.0020(16) -0.0003(16) 0.0082(15) C14 0.0446(19) 0.0488(19) 0.083(3) 0.0022(17) 0.0246(19) 0.0019(15) C15 0.070(2) 0.0498(18) 0.061(2) 0.0062(16) 0.0291(19) 0.0022(17) C16 0.0490(19) 0.0528(18) 0.0481(18) 0.0101(14) 0.0049(15) 0.0007(15) C21 0.065(2) 0.0420(17) 0.068(2) 0.0127(15) 0.0169(18) 0.0128(16) C22 0.049(2) 0.073(2) 0.073(2) 0.0131(18) 0.0252(18) 0.0031(17) N1 0.0370(14) 0.0455(14) 0.0408(15) 0.0042(11) 0.0087(12) 0.0036(11) O1 0.0449(12) 0.0482(11) 0.0446(12) 0.0057(9) 0.0133(10) 0.0012(9) O2 0.0542(13) 0.0561(12) 0.0421(12) -0.0013(9) 0.0125(10) -0.0044(10) O3 0.0339(11) 0.0539(12) 0.0541(13) 0.0148(10) 0.0077(9) 0.0083(9) O4 0.0449(12) 0.0700(14) 0.0483(13) 0.0185(11) 0.0040(10) 0.0125(11) O6 0.0468(12) 0.0601(13) 0.0408(12) 0.0011(10) 0.0055(10) 0.0000(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 O3 1.428(3) . ? C2 O1 1.442(3) . ? C2 C22 1.500(4) . ? C2 C21 1.504(4) . ? C4 O4 1.209(3) . ? C4 O3 1.372(3) . ? C4 C5 1.443(4) . ? C5 C7 1.413(4) . ? C5 C6 1.437(4) . ? C6 O6 1.224(3) . ? C6 O1 1.363(3) . ? C7 N1 1.321(3) . ? C7 O2 1.325(3) . ? C10 O2 1.462(4) . ? C11 C12 1.374(4) . ? C11 C16 1.374(4) . ? C11 N1 1.433(3) . ? C12 C13 1.385(4) . ? C13 C14 1.366(4) . ? C14 C15 1.367(5) . ? C15 C16 1.386(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 C2 O1 109.4(2) . . ? O3 C2 C22 106.6(2) . . ? O1 C2 C22 105.5(2) . . ? O3 C2 C21 111.1(2) . . ? O1 C2 C21 110.4(2) . . ? C22 C2 C21 113.7(3) . . ? O4 C4 O3 116.3(3) . . ? O4 C4 C5 127.4(3) . . ? O3 C4 C5 116.2(2) . . ? C7 C5 C6 119.1(2) . . ? C7 C5 C4 120.7(3) . . ? C6 C5 C4 118.8(2) . . ? O6 C6 O1 115.7(3) . . ? O6 C6 C5 126.9(3) . . ? O1 C6 C5 117.4(2) . . ? N1 C7 O2 113.9(3) . . ? N1 C7 C5 121.9(3) . . ? O2 C7 C5 124.2(2) . . ? C12 C11 C16 119.6(3) . . ? C12 C11 N1 116.1(3) . . ? C16 C11 N1 124.2(3) . . ? C11 C12 C13 120.6(3) . . ? C14 C13 C12 119.3(3) . . ? C13 C14 C15 120.6(3) . . ? C14 C15 C16 120.0(3) . . ? C11 C16 C15 119.8(3) . . ? C7 N1 C11 129.7(3) . . ? C6 O1 C2 118.3(2) . . ? C7 O2 C10 120.7(2) . . ? C4 O3 C2 118.0(2) . . ? 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 O4 C4 C5 C7 2.9(5) . . . . ? O3 C4 C5 C7 179.1(2) . . . . ? O4 C4 C5 C6 -163.4(3) . . . . ? O3 C4 C5 C6 12.8(4) . . . . ? C7 C5 C6 O6 -4.9(4) . . . . ? C4 C5 C6 O6 161.6(3) . . . . ? C7 C5 C6 O1 176.7(2) . . . . ? C4 C5 C6 O1 -16.8(4) . . . . ? C6 C5 C7 N1 15.6(4) . . . . ? C4 C5 C7 N1 -150.7(3) . . . . ? C6 C5 C7 O2 -165.6(3) . . . . ? C4 C5 C7 O2 28.1(4) . . . . ? C16 C11 C12 C13 2.4(4) . . . . ? N1 C11 C12 C13 -179.8(3) . . . . ? C11 C12 C13 C14 -1.0(5) . . . . ? C12 C13 C14 C15 -0.9(5) . . . . ? C13 C14 C15 C16 1.3(5) . . . . ? C12 C11 C16 C15 -2.0(4) . . . . ? N1 C11 C16 C15 -179.5(3) . . . . ? C14 C15 C16 C11 0.2(5) . . . . ? O2 C7 N1 C11 9.3(4) . . . . ? C5 C7 N1 C11 -171.8(3) . . . . ? C12 C11 N1 C7 148.1(3) . . . . ? C16 C11 N1 C7 -34.3(4) . . . . ? O6 C6 O1 C2 167.1(2) . . . . ? C5 C6 O1 C2 -14.3(4) . . . . ? O3 C2 O1 C6 46.7(3) . . . . ? C22 C2 O1 C6 161.0(2) . . . . ? C21 C2 O1 C6 -75.9(3) . . . . ? N1 C7 O2 C10 -142.1(3) . . . . ? C5 C7 O2 C10 39.1(4) . . . . ? O4 C4 O3 C2 -160.9(3) . . . . ? C5 C4 O3 C2 22.4(3) . . . . ? O1 C2 O3 C4 -51.1(3) . . . . ? C22 C2 O3 C4 -164.6(2) . . . . ? C21 C2 O3 C4 71.0(3) . . . . ? #===END # Compound (15) # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-08-06 at 13:20:55 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : cw1168 dreduc struct psi_scan data_cw1168 _database_code_CSD 177780 _audit_creation_date 2001-08-06T13:20:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H16 N2 O4' _chemical_formula_structural 'C13 H16 N2 O4' _chemical_formula_sum 'C14 H16 N2 O4' _chemical_formula_weight 276.29 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.328(2) _cell_length_b 9.1873(9) _cell_length_c 13.049(3) _cell_angle_alpha 90 _cell_angle_beta 110.21(2) _cell_angle_gamma 90 _cell_volume 1387.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_factor_muR 0.02 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 1 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9526 _exptl_absorpt_correction_T_max 0.9806 _exptl_absorpt_correction_T_ave 0.9483 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.11316E-1 _diffrn_orient_matrix_ub_12 0.107852 _diffrn_orient_matrix_ub_13 -0.5215E-2 _diffrn_orient_matrix_ub_21 0.08451 _diffrn_orient_matrix_ub_22 0.14451E-1 _diffrn_orient_matrix_ub_23 0.40123E-1 _diffrn_orient_matrix_ub_31 0.14164E-1 _diffrn_orient_matrix_ub_32 0.206E-3 _diffrn_orient_matrix_ub_33 -0.71023E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -2 _diffrn_standards_decay_corr_max 1.001 _diffrn_standards_decay_corr_min 0.962 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 6 1 1 2 -5 -1 4 0 -6 _diffrn_reflns_number 2423 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_unetI/netI 0.0875 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.953 _diffrn_measured_fraction_theta_max 0.953 _reflns_number_total 2312 _reflns_number_gt 889 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0729P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2312 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1769 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1642 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.167 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C 0.7395(4) 0.1276(4) 0.6331(3) 0.0693(11) Uani 1 1 d . . . C4 C 0.9292(4) 0.1350(4) 0.6244(3) 0.0727(12) Uani 1 1 d . . . C5 C 0.9708(4) 0.0844(4) 0.7354(3) 0.0620(10) Uani 1 1 d . . . C6 C 0.8996(4) 0.1029(4) 0.8002(3) 0.0617(10) Uani 1 1 d . . . C7 C 1.0856(4) 0.0266(4) 0.7827(3) 0.0645(11) Uani 1 1 d . . . C8 C 1.2748(4) 0.0206(4) 0.7538(3) 0.0654(11) Uani 1 1 d . . . C9 C 1.3265(5) -0.0524(4) 0.6898(3) 0.0794(12) Uani 1 1 d . . . H9 H 1.2819 -0.1069 0.63 0.095 Uiso 1 1 calc R . . C10 C 1.4434(5) -0.0436(5) 0.7151(4) 0.0891(14) Uani 1 1 d . . . H10 H 1.4781 -0.093 0.6724 0.107 Uiso 1 1 calc R . . C11 C 1.5107(5) 0.0371(5) 0.8028(4) 0.0915(14) Uani 1 1 d . . . H11 H 1.5904 0.0423 0.8198 0.11 Uiso 1 1 calc R . . C12 C 1.4582(4) 0.1096(5) 0.8645(4) 0.0884(13) Uani 1 1 d . . . H12 H 1.5028 0.1639 0.9244 0.106 Uiso 1 1 calc R . . C13 C 1.3418(4) 0.1033(4) 0.8396(3) 0.0780(12) Uani 1 1 d . . . H13 H 1.3073 0.1555 0.8812 0.094 Uiso 1 1 calc R . . C14 C 1.2150(4) -0.1254(5) 0.9327(3) 0.0916(15) Uani 1 1 d . . . H14A H 1.2243 -0.1402 1.0081 0.137 Uiso 1 1 calc R . . H14B H 1.2859 -0.0892 0.9274 0.137 Uiso 1 1 calc R . . H14C H 1.1954 -0.2161 0.8942 0.137 Uiso 1 1 calc R . . C21 C 0.7150(4) -0.0307(4) 0.6074(3) 0.0818(13) Uani 1 1 d . . . H21A H 0.6815 -0.0433 0.5297 0.123 Uiso 1 1 calc R . . H21B H 0.6621 -0.0652 0.6413 0.123 Uiso 1 1 calc R . . H21C H 0.7858 -0.0849 0.6347 0.123 Uiso 1 1 calc R . . C22 C 0.6355(4) 0.2230(5) 0.5949(4) 0.0967(15) Uani 1 1 d . . . H22A H 0.5987 0.2127 0.5173 0.145 Uiso 1 1 calc R . . H22B H 0.6583 0.3225 0.612 0.145 Uiso 1 1 calc R . . H22C H 0.5824 0.1953 0.6306 0.145 Uiso 1 1 calc R . . N1 N 1.1522(4) 0.0133(4) 0.7206(3) 0.0794(11) Uani 1 1 d . . . N2 N 1.1237(3) -0.0212(4) 0.8852(3) 0.0673(10) Uani 1 1 d . . . O1 O 0.7895(2) 0.1477(3) 0.74961(19) 0.0709(8) Uani 1 1 d . . . O3 O 0.8184(3) 0.1822(3) 0.5841(2) 0.0768(8) Uani 1 1 d . . . O4 O 0.9846(3) 0.1439(4) 0.5623(2) 0.1016(11) Uani 1 1 d . . . O6 O 0.9300(2) 0.0885(3) 0.90023(19) 0.0708(8) Uani 1 1 d . . . H1 H 1.117(3) 0.039(4) 0.655(4) 0.073(13) Uiso 1 1 d . . . H2 H 1.077(3) -0.004(4) 0.915(3) 0.065(14) Uiso 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 C2 0.083(3) 0.068(3) 0.048(2) 0.0037(18) 0.011(2) 0.002(2) C4 0.097(4) 0.076(3) 0.038(2) 0.0088(18) 0.015(2) -0.001(2) C5 0.082(3) 0.065(2) 0.037(2) 0.0027(16) 0.017(2) -0.002(2) C6 0.075(3) 0.057(2) 0.044(2) 0.0004(17) 0.008(2) -0.002(2) C7 0.087(3) 0.070(2) 0.037(2) -0.0009(17) 0.023(2) -0.007(2) C8 0.081(3) 0.071(3) 0.044(2) 0.0045(18) 0.020(2) 0.005(2) C9 0.105(4) 0.083(3) 0.059(3) -0.012(2) 0.039(3) -0.006(3) C10 0.098(4) 0.102(3) 0.075(3) -0.014(3) 0.039(3) 0.013(3) C11 0.082(3) 0.120(4) 0.075(3) -0.005(3) 0.031(3) 0.012(3) C12 0.093(4) 0.110(3) 0.055(3) -0.014(2) 0.017(3) 0.012(3) C13 0.085(3) 0.088(3) 0.061(3) -0.011(2) 0.025(2) 0.013(3) C14 0.119(4) 0.105(3) 0.056(3) 0.029(2) 0.036(3) 0.036(3) C21 0.093(4) 0.077(3) 0.059(3) -0.002(2) 0.006(2) -0.006(2) C22 0.105(4) 0.096(3) 0.071(3) 0.014(2) 0.008(3) 0.029(3) N1 0.086(3) 0.114(3) 0.036(2) 0.0052(18) 0.018(2) 0.003(2) N2 0.080(3) 0.081(2) 0.0419(19) 0.0092(15) 0.0228(19) 0.010(2) O1 0.082(2) 0.0772(17) 0.0462(16) 0.0009(12) 0.0137(14) 0.0140(14) O3 0.095(2) 0.0753(18) 0.0502(16) 0.0175(13) 0.0118(16) 0.0050(16) O4 0.125(3) 0.135(3) 0.0493(18) 0.0303(16) 0.0356(19) 0.016(2) O6 0.0850(19) 0.0918(19) 0.0326(14) 0.0018(11) 0.0168(13) 0.0028(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 O3 1.428(5) . ? C2 O1 1.441(4) . ? C2 C22 1.490(5) . ? C2 C21 1.499(5) . ? C4 O4 1.229(5) . ? C4 O3 1.354(5) . ? C4 C5 1.438(5) . ? C5 C6 1.424(5) . ? C5 C7 1.436(5) . ? C6 O6 1.234(4) . ? C6 O1 1.353(4) . ? C7 N2 1.329(5) . ? C7 N1 1.344(5) . ? C8 C13 1.369(5) . ? C8 C9 1.386(5) . ? C8 N1 1.422(5) . ? C9 C10 1.365(6) . ? C10 C11 1.376(6) . ? C11 C12 1.367(6) . ? C12 C13 1.359(6) . ? C14 N2 1.444(5) . ? 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 O3 C2 O1 108.5(3) . . ? O3 C2 C22 106.5(3) . . ? O1 C2 C22 106.5(3) . . ? O3 C2 C21 110.8(3) . . ? O1 C2 C21 109.9(3) . . ? C22 C2 C21 114.4(4) . . ? O4 C4 O3 116.0(3) . . ? O4 C4 C5 126.8(5) . . ? O3 C4 C5 117.1(4) . . ? C6 C5 C7 120.5(3) . . ? C6 C5 C4 118.8(4) . . ? C7 C5 C4 120.6(4) . . ? O6 C6 O1 115.9(4) . . ? O6 C6 C5 126.2(4) . . ? O1 C6 C5 117.8(3) . . ? N2 C7 N1 120.0(4) . . ? N2 C7 C5 120.5(4) . . ? N1 C7 C5 119.4(3) . . ? C13 C8 C9 119.2(4) . . ? C13 C8 N1 123.5(4) . . ? C9 C8 N1 117.1(4) . . ? C10 C9 C8 119.5(4) . . ? C9 C10 C11 121.1(4) . . ? C12 C11 C10 118.7(5) . . ? C13 C12 C11 120.9(4) . . ? C12 C13 C8 120.5(4) . . ? C7 N1 C8 128.2(4) . . ? C7 N2 C14 127.1(4) . . ? C6 O1 C2 117.9(3) . . ? C4 O3 C2 117.8(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 O4 C4 C5 C6 170.3(4) . . . . ? O3 C4 C5 C6 -7.6(5) . . . . ? O4 C4 C5 C7 -4.9(6) . . . . ? O3 C4 C5 C7 177.2(3) . . . . ? C7 C5 C6 O6 8.4(6) . . . . ? C4 C5 C6 O6 -166.8(3) . . . . ? C7 C5 C6 O1 -175.3(3) . . . . ? C4 C5 C6 O1 9.5(5) . . . . ? C6 C5 C7 N2 5.4(5) . . . . ? C4 C5 C7 N2 -179.5(3) . . . . ? C6 C5 C7 N1 -178.4(3) . . . . ? C4 C5 C7 N1 -3.3(5) . . . . ? C13 C8 C9 C10 1.8(6) . . . . ? N1 C8 C9 C10 177.1(4) . . . . ? C8 C9 C10 C11 -0.4(7) . . . . ? C9 C10 C11 C12 -0.2(7) . . . . ? C10 C11 C12 C13 -0.5(7) . . . . ? C11 C12 C13 C8 1.9(7) . . . . ? C9 C8 C13 C12 -2.5(6) . . . . ? N1 C8 C13 C12 -177.5(4) . . . . ? N2 C7 N1 C8 -33.3(6) . . . . ? C5 C7 N1 C8 150.4(4) . . . . ? C13 C8 N1 C7 -30.7(6) . . . . ? C9 C8 N1 C7 154.2(4) . . . . ? N1 C7 N2 C14 -19.8(6) . . . . ? C5 C7 N2 C14 156.4(4) . . . . ? O6 C6 O1 C2 -163.0(3) . . . . ? C5 C6 O1 C2 20.3(5) . . . . ? O3 C2 O1 C6 -49.2(4) . . . . ? C22 C2 O1 C6 -163.5(3) . . . . ? C21 C2 O1 C6 72.1(4) . . . . ? O4 C4 O3 C2 157.4(3) . . . . ? C5 C4 O3 C2 -24.5(5) . . . . ? O1 C2 O3 C4 51.4(4) . . . . ? C22 C2 O3 C4 165.7(3) . . . . ? C21 C2 O3 C4 -69.4(4) . . . . ? #===END # Compound (16) # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-08-06 at 12:47:28 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 1794r31 dreduc struct psi_scan data_1794r31 _database_code_CSD 177781 _audit_creation_date 2001-08-06T12:47:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H26 N2 O4' _chemical_formula_structural 'C19 H26 N2 O4' _chemical_formula_sum 'C19 H26 N2 O4' _chemical_formula_weight 346.42 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9800(10) _cell_length_b 11.6629(6) _cell_length_c 13.7880(10) _cell_angle_alpha 90 _cell_angle_beta 102.382(9) _cell_angle_gamma 90 _cell_volume 1881.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.33 _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_factor_muR 0.006 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9503 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_correction_T_ave 0.9577 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.67228E-1 _diffrn_orient_matrix_ub_12 -0.7735E-2 _diffrn_orient_matrix_ub_13 -0.31769E-1 _diffrn_orient_matrix_ub_21 -0.52728E-1 _diffrn_orient_matrix_ub_22 -0.6414E-2 _diffrn_orient_matrix_ub_23 -0.66626E-1 _diffrn_orient_matrix_ub_31 0.2128E-2 _diffrn_orient_matrix_ub_32 0.85156E-1 _diffrn_orient_matrix_ub_33 -0.7918E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -2 _diffrn_standards_decay_corr_max 1.011 _diffrn_standards_decay_corr_min 0.943 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -7 1 0 2 1 -8 -1 7 -1 _diffrn_reflns_number 3473 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_unetI/netI 0.0286 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3307 _reflns_number_gt 2214 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0764P)^2^+1.1529P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0053(18) _refine_ls_number_reflns 3307 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.386 _refine_diff_density_min -0.29 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C -0.2289(2) 0.4616(3) 0.1024(2) 0.0511(7) Uani 1 1 d . . . C4 C -0.0920(2) 0.3593(2) 0.03289(18) 0.0425(6) Uani 1 1 d . . . C5 C -0.0609(2) 0.3045(2) 0.12839(17) 0.0381(6) Uani 1 1 d . . . C6 C -0.1500(2) 0.2888(2) 0.1828(2) 0.0454(6) Uani 1 1 d . . . C7 C 0.0465(2) 0.2487(2) 0.15731(18) 0.0399(6) Uani 1 1 d . . . C8 C 0.0644(3) 0.2802(3) 0.3363(2) 0.0659(9) Uani 1 1 d . . . H8A H 0.1055 0.246 0.3969 0.099 Uiso 1 1 calc R . . H8B H -0.0162 0.2754 0.3337 0.099 Uiso 1 1 calc R . . H8C H 0.0862 0.3592 0.3342 0.099 Uiso 1 1 calc R . . C9 C 0.1731(3) 0.1265(3) 0.2797(2) 0.0680(9) Uani 1 1 d . . . H9A H 0.1942 0.1205 0.3507 0.102 Uiso 1 1 calc R . . H9B H 0.24 0.1419 0.2539 0.102 Uiso 1 1 calc R . . H9C H 0.1391 0.0558 0.2524 0.102 Uiso 1 1 calc R . . C10 C 0.2279(2) 0.2278(2) 0.10079(18) 0.0411(6) Uani 1 1 d . . . C11 C 0.2868(2) 0.1520(2) 0.05115(19) 0.0418(6) Uani 1 1 d . . . C12 C 0.4054(2) 0.1653(3) 0.0713(2) 0.0580(8) Uani 1 1 d . . . H12 H 0.4479 0.1171 0.0393 0.07 Uiso 1 1 calc R . . C13 C 0.4628(3) 0.2465(3) 0.1363(3) 0.0705(10) Uani 1 1 d . . . H13 H 0.5421 0.2511 0.1486 0.085 Uiso 1 1 calc R . . C14 C 0.4023(3) 0.3198(3) 0.1824(3) 0.0699(9) Uani 1 1 d . . . H14 H 0.4399 0.375 0.2262 0.084 Uiso 1 1 calc R . . C15 C 0.2849(2) 0.3117(3) 0.1634(2) 0.0563(7) Uani 1 1 d . . . H15 H 0.2434 0.3632 0.1932 0.068 Uiso 1 1 calc R . . C16 C 0.2289(2) 0.0583(2) -0.02071(19) 0.0446(6) Uani 1 1 d . . . C17 C 0.1640(3) -0.0257(3) 0.0322(2) 0.0577(8) Uani 1 1 d . . . H17A H 0.1078 0.0152 0.0588 0.087 Uiso 1 1 calc R . . H17B H 0.2166 -0.0629 0.0851 0.087 Uiso 1 1 calc R . . H17C H 0.1267 -0.0823 -0.0143 0.087 Uiso 1 1 calc R . . C18 C 0.1476(3) 0.1103(3) -0.1119(2) 0.0637(8) Uani 1 1 d . . . H18A H 0.091 0.1563 -0.0905 0.096 Uiso 1 1 calc R . . H18B H 0.1107 0.0498 -0.1541 0.096 Uiso 1 1 calc R . . H18C H 0.1905 0.1573 -0.148 0.096 Uiso 1 1 calc R . . C19 C 0.3165(3) -0.0127(3) -0.0614(2) 0.0642(9) Uani 1 1 d . . . H19A H 0.3693 -0.0478 -0.0073 0.096 Uiso 1 1 calc R . . H19B H 0.3575 0.0364 -0.0975 0.096 Uiso 1 1 calc R . . H19C H 0.2776 -0.0712 -0.1049 0.096 Uiso 1 1 calc R . . C21 C -0.1509(3) 0.5493(3) 0.1620(2) 0.0637(9) Uani 1 1 d . . . H21A H -0.1452 0.6148 0.1211 0.095 Uiso 1 1 calc R . . H21B H -0.0764 0.5165 0.185 0.095 Uiso 1 1 calc R . . H21C H -0.1812 0.5726 0.218 0.095 Uiso 1 1 calc R . . C22 C -0.3484(3) 0.5057(4) 0.0637(3) 0.0801(11) Uani 1 1 d . . . H22A H -0.3455 0.5733 0.0247 0.12 Uiso 1 1 calc R . . H22B H -0.3828 0.5239 0.1186 0.12 Uiso 1 1 calc R . . H22C H -0.3929 0.4479 0.0233 0.12 Uiso 1 1 calc R . . N1 N 0.10571(17) 0.22232(19) 0.08739(17) 0.0419(5) Uani 1 1 d . . . N2 N 0.09109(19) 0.2198(2) 0.25230(15) 0.0493(6) Uani 1 1 d . . . O1 O -0.24052(15) 0.36203(17) 0.15964(14) 0.0533(5) Uani 1 1 d . . . O3 O -0.18699(16) 0.42623(18) 0.01673(13) 0.0546(5) Uani 1 1 d . . . O4 O -0.04627(16) 0.34697(19) -0.03728(13) 0.0600(6) Uani 1 1 d . . . O6 O -0.15554(18) 0.21424(18) 0.24268(16) 0.0634(6) Uani 1 1 d . . . H1 H 0.069(2) 0.243(2) 0.030(2) 0.048(8) Uiso 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 C2 0.0512(16) 0.0573(17) 0.0497(16) 0.0075(14) 0.0215(13) 0.0148(14) C4 0.0364(13) 0.0500(16) 0.0420(14) -0.0044(12) 0.0100(11) 0.0040(12) C5 0.0383(13) 0.0380(14) 0.0391(13) -0.0037(11) 0.0105(10) -0.0009(11) C6 0.0452(15) 0.0457(16) 0.0472(15) -0.0038(13) 0.0143(12) -0.0044(12) C7 0.0420(13) 0.0359(13) 0.0414(13) -0.0058(11) 0.0078(11) -0.0028(11) C8 0.073(2) 0.079(2) 0.0440(16) -0.0139(16) 0.0096(14) -0.0010(17) C9 0.076(2) 0.067(2) 0.0575(18) 0.0154(16) 0.0070(16) 0.0163(18) C10 0.0361(13) 0.0427(14) 0.0427(14) 0.0016(12) 0.0043(10) 0.0003(11) C11 0.0347(13) 0.0433(15) 0.0471(14) 0.0057(12) 0.0084(11) 0.0035(11) C12 0.0363(14) 0.0614(19) 0.076(2) 0.0031(16) 0.0107(13) 0.0065(14) C13 0.0343(15) 0.081(2) 0.088(2) 0.008(2) -0.0045(15) -0.0063(16) C14 0.0539(19) 0.069(2) 0.077(2) -0.0078(18) -0.0074(16) -0.0134(17) C15 0.0530(17) 0.0524(17) 0.0602(17) -0.0097(14) 0.0048(14) -0.0032(14) C16 0.0409(14) 0.0474(15) 0.0462(15) -0.0025(12) 0.0109(11) 0.0069(12) C17 0.0549(17) 0.0472(17) 0.074(2) -0.0099(15) 0.0204(15) -0.0031(14) C18 0.0656(19) 0.072(2) 0.0482(16) -0.0100(15) 0.0002(14) 0.0141(17) C19 0.0622(19) 0.065(2) 0.071(2) -0.0079(16) 0.0272(16) 0.0124(16) C21 0.080(2) 0.0512(18) 0.0669(19) -0.0034(15) 0.0308(17) 0.0068(16) C22 0.062(2) 0.108(3) 0.074(2) 0.015(2) 0.0237(17) 0.039(2) N1 0.0354(11) 0.0478(13) 0.0416(12) -0.0057(10) 0.0060(10) 0.0059(10) N2 0.0519(13) 0.0551(14) 0.0391(12) -0.0009(11) 0.0057(10) 0.0061(11) O1 0.0419(10) 0.0608(12) 0.0627(12) 0.0065(10) 0.0232(9) 0.0054(9) O3 0.0509(11) 0.0731(14) 0.0413(10) 0.0038(9) 0.0131(8) 0.0211(10) O4 0.0545(11) 0.0879(16) 0.0410(10) 0.0034(10) 0.0179(9) 0.0218(11) O6 0.0677(13) 0.0557(13) 0.0733(14) 0.0179(11) 0.0296(11) -0.0041(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 O1 1.428(3) . ? C2 O3 1.439(3) . ? C2 C21 1.506(4) . ? C2 C22 1.507(4) . ? C4 O4 1.218(3) . ? C4 O3 1.358(3) . ? C4 C5 1.439(3) . ? C5 C7 1.421(3) . ? C5 C6 1.441(3) . ? C6 O6 1.211(3) . ? C6 O1 1.363(3) . ? C7 N2 1.347(3) . ? C7 N1 1.349(3) . ? C8 N2 1.449(4) . ? C9 N2 1.461(4) . ? C10 C15 1.384(4) . ? C10 C11 1.399(3) . ? C10 N1 1.437(3) . ? C11 C12 1.396(4) . ? C11 C16 1.537(4) . ? C12 C13 1.382(5) . ? C13 C14 1.363(5) . ? C14 C15 1.377(4) . ? C16 C17 1.530(4) . ? C16 C19 1.535(4) . ? C16 C18 1.541(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 O3 108.2(2) . . ? O1 C2 C21 111.9(2) . . ? O3 C2 C21 111.0(2) . . ? O1 C2 C22 105.9(2) . . ? O3 C2 C22 106.2(2) . . ? C21 C2 C22 113.1(3) . . ? O4 C4 O3 116.2(2) . . ? O4 C4 C5 127.0(2) . . ? O3 C4 C5 116.7(2) . . ? C7 C5 C4 120.1(2) . . ? C7 C5 C6 121.5(2) . . ? C4 C5 C6 117.2(2) . . ? O6 C6 O1 116.9(2) . . ? O6 C6 C5 126.9(3) . . ? O1 C6 C5 116.1(2) . . ? N2 C7 N1 118.6(2) . . ? N2 C7 C5 122.3(2) . . ? N1 C7 C5 119.2(2) . . ? C15 C10 C11 121.3(2) . . ? C15 C10 N1 117.7(2) . . ? C11 C10 N1 121.1(2) . . ? C12 C11 C10 115.5(3) . . ? C12 C11 C16 120.5(2) . . ? C10 C11 C16 124.0(2) . . ? C13 C12 C11 123.3(3) . . ? C14 C13 C12 119.5(3) . . ? C13 C14 C15 119.5(3) . . ? C14 C15 C10 120.9(3) . . ? C17 C16 C19 106.6(2) . . ? C17 C16 C11 110.7(2) . . ? C19 C16 C11 111.7(2) . . ? C17 C16 C18 110.1(2) . . ? C19 C16 C18 106.0(2) . . ? C11 C16 C18 111.4(2) . . ? C7 N1 C10 125.1(2) . . ? C7 N2 C8 123.2(2) . . ? C7 N2 C9 122.8(2) . . ? C8 N2 C9 114.0(2) . . ? C6 O1 C2 118.12(19) . . ? C4 O3 C2 117.21(19) . . ? 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 O4 C4 C5 C7 14.9(4) . . . . ? O3 C4 C5 C7 -169.7(2) . . . . ? O4 C4 C5 C6 -152.9(3) . . . . ? O3 C4 C5 C6 22.5(3) . . . . ? C7 C5 C6 O6 -15.7(4) . . . . ? C4 C5 C6 O6 151.9(3) . . . . ? C7 C5 C6 O1 168.4(2) . . . . ? C4 C5 C6 O1 -24.0(3) . . . . ? C4 C5 C7 N2 164.2(2) . . . . ? C6 C5 C7 N2 -28.5(4) . . . . ? C4 C5 C7 N1 -16.5(4) . . . . ? C6 C5 C7 N1 150.7(2) . . . . ? C15 C10 C11 C12 1.5(4) . . . . ? N1 C10 C11 C12 -179.3(2) . . . . ? C15 C10 C11 C16 -178.9(3) . . . . ? N1 C10 C11 C16 0.2(4) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? C16 C11 C12 C13 -178.9(3) . . . . ? C11 C12 C13 C14 -1.5(5) . . . . ? C12 C13 C14 C15 0.1(5) . . . . ? C13 C14 C15 C10 2.0(5) . . . . ? C11 C10 C15 C14 -2.9(4) . . . . ? N1 C10 C15 C14 177.9(3) . . . . ? C12 C11 C16 C17 119.5(3) . . . . ? C10 C11 C16 C17 -60.0(3) . . . . ? C12 C11 C16 C19 0.8(4) . . . . ? C10 C11 C16 C19 -178.7(2) . . . . ? C12 C11 C16 C18 -117.6(3) . . . . ? C10 C11 C16 C18 62.9(3) . . . . ? N2 C7 N1 C10 -37.6(4) . . . . ? C5 C7 N1 C10 143.1(2) . . . . ? C15 C10 N1 C7 -32.7(4) . . . . ? C11 C10 N1 C7 148.1(3) . . . . ? N1 C7 N2 C8 154.0(3) . . . . ? C5 C7 N2 C8 -26.8(4) . . . . ? N1 C7 N2 C9 -24.4(4) . . . . ? C5 C7 N2 C9 154.9(3) . . . . ? O6 C6 O1 C2 169.8(2) . . . . ? C5 C6 O1 C2 -13.9(3) . . . . ? O3 C2 O1 C6 50.3(3) . . . . ? C21 C2 O1 C6 -72.4(3) . . . . ? C22 C2 O1 C6 163.9(2) . . . . ? O4 C4 O3 C2 -167.5(2) . . . . ? C5 C4 O3 C2 16.6(3) . . . . ? O1 C2 O3 C4 -51.7(3) . . . . ? C21 C2 O3 C4 71.5(3) . . . . ? C22 C2 O3 C4 -165.1(3) . . . . ? #===END # Compound (17).H2O # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-10-16 at 10:42:04 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 1072dm6 data_1072dm6 _database_code_CSD 177782 _audit_creation_date 2001-10-16T10:42:04-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C15 H20 N2 O5' _chemical_formula_weight 308.33 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 8.443(5) _cell_length_b 8.935(5) _cell_length_c 10.454(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 97.780(5) _cell_angle_gamma 90.000(5) _cell_volume 781.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.27 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.9738 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 1487 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.14 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 1487 _reflns_number_gt 1190 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0935P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.042(10) _refine_ls_number_reflns 1487 _refine_ls_number_parameters 212 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1382 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_diff_density_max 0.196 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C 0.1150(8) 0.5501(6) 0.6704(7) 0.0749(19) Uani 1 1 d . . . C4 C 0.1546(5) 0.2923(5) 0.6286(4) 0.0448(10) Uani 1 1 d . . . C5 C 0.2944(5) 0.3372(5) 0.5751(4) 0.0407(10) Uani 1 1 d . . . C6 C 0.3129(6) 0.4861(5) 0.5362(5) 0.0446(10) Uani 1 1 d . . . C7 C 0.4079(5) 0.2242(4) 0.5446(4) 0.0396(10) Uani 1 1 d . . . C8 C 0.2038(5) 0.0890(5) 0.4030(4) 0.0427(10) Uani 1 1 d . . . C9 C 0.1156(6) -0.0383(5) 0.4193(5) 0.0545(12) Uani 1 1 d . . . H9 H 0.1567 -0.1127 0.4766 0.065 Uiso 1 1 calc R . . C10 C -0.0338(7) -0.0533(6) 0.3496(6) 0.0648(15) Uani 1 1 d . . . H10 H -0.0944 -0.1382 0.3602 0.078 Uiso 1 1 calc R . . C11 C -0.0938(7) 0.0554(7) 0.2650(5) 0.0664(15) Uani 1 1 d . . . H11 H -0.1961 0.0458 0.22 0.08 Uiso 1 1 calc R . . C12 C -0.0033(7) 0.1788(6) 0.2462(5) 0.0630(14) Uani 1 1 d . . . H12 H -0.0423 0.2506 0.1856 0.076 Uiso 1 1 calc R . . C13 C 0.1443(6) 0.1963(6) 0.3164(5) 0.0513(12) Uani 1 1 d . . . H13 H 0.2043 0.2814 0.3052 0.062 Uiso 1 1 calc R . . C14 C 0.6778(6) 0.1326(6) 0.5451(6) 0.0634(14) Uani 1 1 d . . . H14A H 0.7833 0.16 0.5842 0.095 Uiso 1 1 calc R . . H14B H 0.6728 0.1354 0.4529 0.095 Uiso 1 1 calc R . . H14C H 0.6536 0.0333 0.5718 0.095 Uiso 1 1 calc R . . C15 C 0.6268(7) 0.3501(6) 0.6810(6) 0.0656(14) Uani 1 1 d . . . H15A H 0.5993 0.4486 0.6486 0.098 Uiso 1 1 calc R . . H15B H 0.7411 0.3404 0.6968 0.098 Uiso 1 1 calc R . . H15C H 0.5831 0.3346 0.7601 0.098 Uiso 1 1 calc R . . C21 C -0.0219(11) 0.6535(8) 0.6600(12) 0.129(4) Uani 1 1 d . . . H21A H 0.0161 0.7539 0.6757 0.193 Uiso 1 1 calc R . . H21B H -0.0904 0.6268 0.7225 0.193 Uiso 1 1 calc R . . H21C H -0.0806 0.6471 0.5748 0.193 Uiso 1 1 calc R . . C22 C 0.2146(10) 0.5527(8) 0.8020(7) 0.100(3) Uani 1 1 d . . . H22A H 0.2999 0.4813 0.8041 0.15 Uiso 1 1 calc R . . H22B H 0.1486 0.5276 0.8668 0.15 Uiso 1 1 calc R . . H22C H 0.2586 0.651 0.8187 0.15 Uiso 1 1 calc R . . N1 N 0.3576(5) 0.1039(4) 0.4740(4) 0.0421(9) Uani 1 1 d . . . H1 H 0.406(7) 0.028(6) 0.482(5) 0.046(14) Uiso 1 1 d . . . N2 N 0.5612(5) 0.2382(4) 0.5856(4) 0.0485(9) Uani 1 1 d . . . O1 O 0.2078(4) 0.5894(3) 0.5707(4) 0.0629(10) Uani 1 1 d . . . O3 O 0.0514(4) 0.4026(4) 0.6475(4) 0.0625(10) Uani 1 1 d . . . O4 O 0.1182(4) 0.1662(4) 0.6577(3) 0.0520(9) Uani 1 1 d . . . O6 O 0.4136(4) 0.5330(3) 0.4726(3) 0.0584(9) Uani 1 1 d . . . O20 O -0.0025(6) 0.1686(4) 0.9040(5) 0.0729(12) Uani 1 1 d . . . H21 H -0.001(8) 0.176(7) 0.820(7) 0.071(18) Uiso 1 1 d . . . H22 H -0.015(11) 0.270(10) 0.940(8) 0.12(3) Uiso 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 C2 0.079(4) 0.042(3) 0.119(5) -0.022(3) 0.071(4) -0.014(3) C4 0.043(2) 0.041(2) 0.053(3) -0.006(2) 0.016(2) 0.000(2) C5 0.038(2) 0.037(2) 0.050(2) -0.0057(18) 0.0162(19) -0.0058(18) C6 0.045(2) 0.037(2) 0.055(2) -0.0047(18) 0.020(2) 0.000(2) C7 0.040(3) 0.037(2) 0.045(2) 0.0029(19) 0.0158(19) -0.0009(18) C8 0.044(3) 0.041(2) 0.043(2) -0.0052(19) 0.008(2) 0.0039(19) C9 0.064(3) 0.039(2) 0.060(3) -0.004(2) 0.012(3) -0.003(2) C10 0.061(3) 0.055(3) 0.079(3) -0.014(3) 0.011(3) -0.015(3) C11 0.052(3) 0.077(4) 0.068(3) -0.030(3) 0.001(3) 0.008(3) C12 0.067(4) 0.066(3) 0.054(3) -0.006(3) 0.002(3) 0.019(3) C13 0.052(3) 0.049(3) 0.056(3) 0.000(2) 0.018(2) 0.009(2) C14 0.036(3) 0.060(3) 0.098(4) 0.008(3) 0.022(3) 0.008(2) C15 0.049(3) 0.066(3) 0.082(4) -0.004(3) 0.008(3) -0.018(3) C21 0.126(7) 0.055(4) 0.233(11) -0.001(5) 0.127(8) 0.017(4) C22 0.136(7) 0.088(4) 0.092(5) -0.049(4) 0.076(5) -0.061(5) N1 0.0379(19) 0.033(2) 0.057(2) 0.0029(17) 0.0111(17) 0.0057(17) N2 0.037(2) 0.044(2) 0.066(2) 0.0053(18) 0.0127(17) -0.0024(16) O1 0.070(2) 0.0316(15) 0.097(3) -0.0041(16) 0.050(2) 0.0023(15) O3 0.056(2) 0.0397(18) 0.101(3) -0.0116(17) 0.042(2) -0.0057(15) O4 0.055(2) 0.0422(18) 0.064(2) -0.0018(15) 0.0258(16) -0.0097(15) O6 0.065(2) 0.0421(17) 0.078(2) 0.0029(16) 0.0437(19) -0.0018(16) O20 0.105(3) 0.045(2) 0.077(3) 0.0047(18) 0.043(2) -0.003(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 O3 1.431(6) . ? C2 O1 1.430(6) . ? C2 C21 1.472(10) . ? C2 C22 1.513(12) . ? C4 O4 1.218(5) . ? C4 O3 1.348(6) . ? C4 C5 1.430(6) . ? C5 C6 1.406(6) . ? C5 C7 1.457(6) . ? C6 O6 1.223(5) . ? C6 O1 1.362(6) . ? C7 N2 1.313(6) . ? C7 N1 1.340(6) . ? C8 C13 1.367(7) . ? C8 C9 1.383(6) . ? C8 N1 1.412(6) . ? C9 C10 1.375(8) . ? C10 C11 1.365(8) . ? C11 C12 1.370(9) . ? C12 C13 1.367(8) . ? C14 N2 1.466(6) . ? C15 N2 1.467(7) . ? 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 O3 C2 O1 109.5(4) . . ? O3 C2 C21 107.0(6) . . ? O1 C2 C21 107.1(6) . . ? O3 C2 C22 108.4(6) . . ? O1 C2 C22 111.5(5) . . ? C21 C2 C22 113.1(7) . . ? O4 C4 O3 116.7(4) . . ? O4 C4 C5 127.4(4) . . ? O3 C4 C5 115.9(4) . . ? C6 C5 C4 120.5(4) . . ? C6 C5 C7 119.4(4) . . ? C4 C5 C7 119.5(4) . . ? O6 C6 O1 116.0(4) . . ? O6 C6 C5 126.4(4) . . ? O1 C6 C5 117.6(4) . . ? N2 C7 N1 118.8(4) . . ? N2 C7 C5 120.7(4) . . ? N1 C7 C5 120.5(4) . . ? C13 C8 C9 120.2(4) . . ? C13 C8 N1 120.8(4) . . ? C9 C8 N1 119.0(4) . . ? C10 C9 C8 119.1(5) . . ? C11 C10 C9 120.5(5) . . ? C10 C11 C12 120.0(5) . . ? C13 C12 C11 120.0(5) . . ? C12 C13 C8 120.1(5) . . ? C7 N1 C8 124.4(4) . . ? C7 N2 C14 121.0(4) . . ? C7 N2 C15 123.5(4) . . ? C14 N2 C15 115.3(4) . . ? C6 O1 C2 117.9(4) . . ? C4 O3 C2 117.6(4) . . ? 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 O4 C4 C5 C6 174.6(5) . . . . ? O3 C4 C5 C6 -4.8(6) . . . . ? O4 C4 C5 C7 2.9(7) . . . . ? O3 C4 C5 C7 -176.5(4) . . . . ? C4 C5 C6 O6 -168.4(5) . . . . ? C7 C5 C6 O6 3.3(7) . . . . ? C4 C5 C6 O1 10.7(6) . . . . ? C7 C5 C6 O1 -177.6(4) . . . . ? C6 C5 C7 N2 58.7(6) . . . . ? C4 C5 C7 N2 -129.6(4) . . . . ? C6 C5 C7 N1 -121.3(5) . . . . ? C4 C5 C7 N1 50.5(5) . . . . ? C13 C8 C9 C10 -1.6(7) . . . . ? N1 C8 C9 C10 -179.6(5) . . . . ? C8 C9 C10 C11 0.4(8) . . . . ? C9 C10 C11 C12 1.8(8) . . . . ? C10 C11 C12 C13 -2.9(8) . . . . ? C11 C12 C13 C8 1.7(7) . . . . ? C9 C8 C13 C12 0.5(6) . . . . ? N1 C8 C13 C12 178.5(4) . . . . ? N2 C7 N1 C8 -166.9(4) . . . . ? C5 C7 N1 C8 13.1(6) . . . . ? C13 C8 N1 C7 53.0(6) . . . . ? C9 C8 N1 C7 -129.0(5) . . . . ? N1 C7 N2 C14 5.8(6) . . . . ? C5 C7 N2 C14 -174.1(4) . . . . ? N1 C7 N2 C15 -169.2(4) . . . . ? C5 C7 N2 C15 10.9(6) . . . . ? O6 C6 O1 C2 -164.6(5) . . . . ? C5 C6 O1 C2 16.2(7) . . . . ? O3 C2 O1 C6 -45.7(7) . . . . ? C21 C2 O1 C6 -161.4(6) . . . . ? C22 C2 O1 C6 74.3(6) . . . . ? O4 C4 O3 C2 152.8(5) . . . . ? C5 C4 O3 C2 -27.8(7) . . . . ? O1 C2 O3 C4 52.2(7) . . . . ? C21 C2 O3 C4 168.0(6) . . . . ? C22 C2 O3 C4 -69.7(6) . . . . ? #===END # Compound (18).THF # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-10-16 at 10:45:31 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 975dm1 data_975dm1 _database_code_CSD 177783 _audit_creation_date 2001-10-16T10:45:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C22 H32 N2 O5' _chemical_formula_weight 404.5 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 29.650(10) _cell_length_b 12.6560(10) _cell_length_c 12.512(5) _cell_angle_alpha 90 _cell_angle_beta 109.44(2) _cell_angle_gamma 90 _cell_volume 4427(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_min 0.9503 _exptl_absorpt_correction_T_max 0.9747 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 3964 _diffrn_reflns_av_R_equivalents 0.0132 _diffrn_reflns_av_unetI/netI 0.0396 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3885 _reflns_number_gt 2062 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1694P)^2^+3.4633P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0024(11) _refine_ls_number_reflns 3885 _refine_ls_number_parameters 265 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.1427 _refine_ls_R_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.2972 _refine_ls_wR_factor_gt 0.2446 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.098 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.22245(12) 0.7802(2) 0.2269(3) 0.0559(9) Uani 1 1 d . . . N2 N 0.26655(11) 0.6770(2) 0.3739(3) 0.0600(9) Uani 1 1 d . . . C2 C 0.10142(16) 0.5158(4) 0.1938(4) 0.0764(13) Uani 1 1 d . . . C4 C 0.18744(15) 0.5170(3) 0.2557(3) 0.0589(10) Uani 1 1 d . . . C5 C 0.18418(13) 0.6270(3) 0.2740(3) 0.0533(10) Uani 1 1 d . . . C6 C 0.14239(15) 0.6712(3) 0.2868(4) 0.0673(11) Uani 1 1 d . . . C7 C 0.22575(13) 0.6954(3) 0.2923(3) 0.0525(9) Uani 1 1 d . . . C8 C 0.18548(14) 0.7993(3) 0.1210(3) 0.0567(10) Uani 1 1 d . . . C9 C 0.15577(16) 0.8867(3) 0.1110(4) 0.0683(12) Uani 1 1 d . . . C10 C 0.12135(17) 0.9061(4) 0.0061(5) 0.0828(14) Uani 1 1 d . . . H10 H 0.1016 0.9647 -0.0022 0.099 Uiso 1 1 calc R . . C11 C 0.11556(17) 0.8409(5) -0.0866(4) 0.0839(14) Uani 1 1 d . . . C12 C 0.14674(17) 0.7579(4) -0.0741(4) 0.0772(13) Uani 1 1 d . . . H12 H 0.144 0.7153 -0.1365 0.093 Uiso 1 1 calc R . . C13 C 0.18231(15) 0.7351(3) 0.0281(4) 0.0633(11) Uani 1 1 d . . . C14 C 0.16132(19) 0.9613(4) 0.2108(5) 0.0863(15) Uani 1 1 d . . . H14A H 0.1379 1.0165 0.1877 0.13 Uiso 1 1 calc R . . H14B H 0.1928 0.9916 0.2349 0.13 Uiso 1 1 calc R . . H14C H 0.1568 0.9224 0.2723 0.13 Uiso 1 1 calc R . . C15 C 0.0761(2) 0.8622(6) -0.1978(5) 0.122(2) Uani 1 1 d . . . H15A H 0.0582 0.9231 -0.19 0.183 Uiso 1 1 calc R . . H15B H 0.0553 0.8021 -0.2179 0.183 Uiso 1 1 calc R . . H15C H 0.0899 0.8748 -0.2561 0.183 Uiso 1 1 calc R . . C16 C 0.21584(18) 0.6448(4) 0.0355(4) 0.0793(13) Uani 1 1 d . . . H16A H 0.238 0.6398 0.1114 0.119 Uiso 0.5 1 calc PR . . H16B H 0.2331 0.6564 -0.0162 0.119 Uiso 0.5 1 calc PR . . H16C H 0.1979 0.5803 0.016 0.119 Uiso 0.5 1 calc PR . . H16D H 0.208 0.6112 -0.0372 0.119 Uiso 0.5 1 calc PR . . H16E H 0.2129 0.5946 0.0903 0.119 Uiso 0.5 1 calc PR . . H16F H 0.2481 0.6707 0.0581 0.119 Uiso 0.5 1 calc PR . . C17 C 0.30989(15) 0.7352(4) 0.3815(4) 0.0803(14) Uani 1 1 d . . . H17A H 0.3358 0.7106 0.4457 0.12 Uiso 0.5 1 calc PR . . H17B H 0.3048 0.8091 0.3901 0.12 Uiso 0.5 1 calc PR . . H17C H 0.3176 0.7241 0.3136 0.12 Uiso 0.5 1 calc PR . . H17D H 0.303 0.7853 0.3206 0.12 Uiso 0.5 1 calc PR . . H17E H 0.334 0.6867 0.3762 0.12 Uiso 0.5 1 calc PR . . H17F H 0.3212 0.7718 0.4527 0.12 Uiso 0.5 1 calc PR . . C18 C 0.27061(17) 0.6022(3) 0.4660(4) 0.0739(13) Uani 1 1 d . . . H18A H 0.3031 0.6 0.5161 0.111 Uiso 0.5 1 calc PR . . H18B H 0.2611 0.5331 0.4349 0.111 Uiso 0.5 1 calc PR . . H18C H 0.2502 0.6244 0.5074 0.111 Uiso 0.5 1 calc PR . . H18D H 0.2398 0.5716 0.4561 0.111 Uiso 0.5 1 calc PR . . H18E H 0.2818 0.6386 0.5373 0.111 Uiso 0.5 1 calc PR . . H18F H 0.2928 0.5473 0.4649 0.111 Uiso 0.5 1 calc PR . . C21 C 0.0913(2) 0.5469(5) 0.0710(5) 0.1038(19) Uani 1 1 d . . . H21A H 0.0614 0.584 0.0438 0.156 Uiso 1 1 calc R . . H21B H 0.0896 0.4845 0.0262 0.156 Uiso 1 1 calc R . . H21C H 0.1165 0.5918 0.0652 0.156 Uiso 1 1 calc R . . C22 C 0.06400(19) 0.4427(5) 0.2114(6) 0.1073(19) Uani 1 1 d . . . H22A H 0.0333 0.4764 0.1846 0.161 Uiso 1 1 calc R . . H22B H 0.072 0.4272 0.2907 0.161 Uiso 1 1 calc R . . H22C H 0.063 0.3783 0.1702 0.161 Uiso 1 1 calc R . . O1 O 0.10306(11) 0.6062(2) 0.2628(3) 0.0832(10) Uani 1 1 d . . . O3 O 0.14588(10) 0.4601(2) 0.2350(3) 0.0721(9) Uani 1 1 d . . . O6 O 0.13839(12) 0.7578(2) 0.3244(3) 0.0871(10) Uani 1 1 d . . . O4 O 0.22297(11) 0.4676(2) 0.2583(3) 0.0730(9) Uani 1 1 d . . . O2A O 0.0510(10) 0.1543(19) 1.005(2) 0.309(11) Uiso 0.5 1 d PD A 1 C1A C 0.0565(6) 0.2518(16) 0.9657(18) 0.153(6) Uiso 0.5 1 d PD A 1 H1A1 H 0.0582 0.2489 0.8896 0.184 Uiso 0.5 1 calc PR A 1 H1A2 H 0.0843 0.2882 1.0155 0.184 Uiso 0.5 1 calc PR A 1 C2A C 0.0128(6) 0.2985(14) 0.9677(17) 0.155(6) Uiso 0.5 1 d PD A 1 H2A1 H 0.0185 0.341 1.0354 0.185 Uiso 0.5 1 calc PR A 1 H2A2 H -0.0008 0.3431 0.9018 0.185 Uiso 0.5 1 calc PR A 1 C3A C -0.0173(7) 0.2161(15) 0.967(2) 0.165(7) Uiso 0.5 1 d PD A 1 H3A1 H -0.0314 0.2276 1.0258 0.198 Uiso 0.5 1 calc PR A 1 H3A2 H -0.0431 0.2152 0.8948 0.198 Uiso 0.5 1 calc PR A 1 C4A C 0.0041(10) 0.124(2) 0.983(3) 0.212(10) Uiso 0.5 1 d PD A 1 H4A1 H -0.0071 0.0795 0.9162 0.254 Uiso 0.5 1 calc PR A 1 H4A2 H -0.0001 0.0865 1.0471 0.254 Uiso 0.5 1 calc PR A 1 O2B O 0.0571(7) 0.183(2) 0.923(2) 0.284(10) Uiso 0.5 1 d PD B 2 C1B C 0.0183(12) 0.140(3) 0.837(3) 0.47(4) Uiso 0.5 1 d PD B 2 H1B1 H 0.0254 0.0695 0.8162 0.561 Uiso 0.5 1 calc PR B 2 H1B2 H 0.0088 0.1846 0.7704 0.561 Uiso 0.5 1 calc PR B 2 C2B C -0.0178(9) 0.137(2) 0.890(3) 0.225(11) Uiso 0.5 1 d PD B 2 H2B1 H -0.0495 0.1284 0.8353 0.27 Uiso 0.5 1 calc PR B 2 H2B2 H -0.0118 0.0813 0.9467 0.27 Uiso 0.5 1 calc PR B 2 C3B C -0.0113(14) 0.238(3) 0.940(5) 0.59(7) Uiso 0.5 1 d PD B 2 H3B1 H -0.0015 0.2347 1.0224 0.702 Uiso 0.5 1 calc PR B 2 H3B2 H -0.0397 0.2817 0.9114 0.702 Uiso 0.5 1 calc PR B 2 C4B C 0.0268(10) 0.2744(18) 0.902(3) 0.235(12) Uiso 0.5 1 d PD B 2 H4B1 H 0.0152 0.2923 0.822 0.281 Uiso 0.5 1 calc PR B 2 H4B2 H 0.0432 0.335 0.9452 0.281 Uiso 0.5 1 calc PR B 2 H1 H 0.2451(19) 0.823(4) 0.250(5) 0.093(17) Uiso 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 0.060(2) 0.0383(17) 0.067(2) -0.0007(15) 0.0182(17) -0.0038(15) N2 0.063(2) 0.0466(17) 0.066(2) -0.0006(15) 0.0147(17) -0.0013(15) C2 0.064(3) 0.071(3) 0.090(3) 0.002(3) 0.020(2) -0.014(2) C4 0.065(2) 0.044(2) 0.066(2) 0.0019(18) 0.021(2) -0.005(2) C5 0.059(2) 0.0386(19) 0.064(2) -0.0012(17) 0.0224(18) 0.0005(17) C6 0.068(3) 0.058(2) 0.079(3) 0.000(2) 0.028(2) -0.001(2) C7 0.061(2) 0.0384(19) 0.061(2) -0.0084(17) 0.0231(19) 0.0030(17) C8 0.059(2) 0.044(2) 0.068(3) 0.0033(18) 0.024(2) -0.0017(17) C9 0.072(3) 0.052(2) 0.082(3) 0.005(2) 0.028(2) 0.004(2) C10 0.069(3) 0.068(3) 0.107(4) 0.017(3) 0.023(3) 0.013(2) C11 0.073(3) 0.094(4) 0.081(3) 0.017(3) 0.021(3) -0.008(3) C12 0.085(3) 0.080(3) 0.068(3) 0.003(2) 0.027(3) -0.013(3) C13 0.071(3) 0.054(2) 0.070(3) 0.001(2) 0.030(2) -0.004(2) C14 0.097(4) 0.057(3) 0.108(4) -0.003(3) 0.038(3) 0.019(2) C15 0.099(4) 0.153(6) 0.092(4) 0.028(4) 0.003(3) 0.000(4) C16 0.101(3) 0.064(3) 0.084(3) -0.007(2) 0.046(3) 0.004(2) C17 0.062(3) 0.064(3) 0.101(4) 0.005(2) 0.009(2) -0.012(2) C18 0.088(3) 0.057(2) 0.068(3) 0.004(2) 0.014(2) 0.000(2) C21 0.092(4) 0.102(4) 0.097(4) 0.009(3) 0.005(3) -0.024(3) C22 0.082(4) 0.100(4) 0.138(5) 0.004(4) 0.035(3) -0.027(3) O1 0.0658(19) 0.072(2) 0.118(3) -0.0051(19) 0.0386(18) -0.0069(16) O3 0.0758(19) 0.0478(15) 0.090(2) 0.0025(14) 0.0237(16) -0.0120(14) O6 0.089(2) 0.0626(19) 0.125(3) -0.0193(19) 0.055(2) 0.0034(16) O4 0.078(2) 0.0411(14) 0.100(2) -0.0010(14) 0.0299(17) 0.0064(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C7 1.333(5) . ? N1 C8 1.432(5) . ? N2 C7 1.319(5) . ? N2 C17 1.457(5) . ? N2 C18 1.465(5) . ? C2 O1 1.424(6) . ? C2 O3 1.431(5) . ? C2 C21 1.516(7) . ? C2 C22 1.516(6) . ? C4 O4 1.216(5) . ? C4 O3 1.375(5) . ? C4 C5 1.420(5) . ? C5 C6 1.416(5) . ? C5 C7 1.461(5) . ? C6 O6 1.215(5) . ? C6 O1 1.376(5) . ? C8 C9 1.394(6) . ? C8 C13 1.395(6) . ? C9 C10 1.390(7) . ? C9 C14 1.529(7) . ? C10 C11 1.387(7) . ? C11 C12 1.373(7) . ? C11 C15 1.514(7) . ? C12 C13 1.391(7) . ? C13 C16 1.497(6) . ? O2A C1A 1.360(18) . ? O2A C4A 1.380(18) . ? C1A C2A 1.430(17) . ? C2A C3A 1.372(18) . ? C3A C4A 1.315(17) . ? O2B C1B 1.40(2) . ? O2B C4B 1.438(19) . ? C1B C2B 1.43(2) . ? C1B C4B 1.87(4) . ? C2B C3B 1.41(2) . ? C3B C4B 1.44(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C8 125.6(3) . . ? C7 N2 C17 121.5(3) . . ? C7 N2 C18 122.5(3) . . ? C17 N2 C18 115.8(3) . . ? O1 C2 O3 109.6(3) . . ? O1 C2 C21 111.2(4) . . ? O3 C2 C21 109.9(4) . . ? O1 C2 C22 106.3(4) . . ? O3 C2 C22 106.1(4) . . ? C21 C2 C22 113.5(4) . . ? O4 C4 O3 116.7(3) . . ? O4 C4 C5 127.2(4) . . ? O3 C4 C5 116.0(4) . . ? C6 C5 C4 121.0(4) . . ? C6 C5 C7 118.2(3) . . ? C4 C5 C7 120.5(3) . . ? O6 C6 O1 116.1(4) . . ? O6 C6 C5 127.0(4) . . ? O1 C6 C5 116.7(4) . . ? N2 C7 N1 118.6(3) . . ? N2 C7 C5 121.7(3) . . ? N1 C7 C5 119.7(4) . . ? C9 C8 C13 121.5(4) . . ? C9 C8 N1 118.9(4) . . ? C13 C8 N1 119.4(4) . . ? C10 C9 C8 117.9(4) . . ? C10 C9 C14 120.5(4) . . ? C8 C9 C14 121.6(4) . . ? C11 C10 C9 122.2(4) . . ? C12 C11 C10 117.9(4) . . ? C12 C11 C15 121.7(6) . . ? C10 C11 C15 120.4(5) . . ? C11 C12 C13 122.7(5) . . ? C12 C13 C8 117.7(4) . . ? C12 C13 C16 120.0(4) . . ? C8 C13 C16 122.3(4) . . ? C6 O1 C2 117.9(3) . . ? C4 O3 C2 118.0(3) . . ? C1A O2A C4A 115(2) . . ? O2A C1A C2A 98.7(18) . . ? C3A C2A C1A 106.1(17) . . ? C4A C3A C2A 113(2) . . ? C3A C4A O2A 101(2) . . ? C1B O2B C4B 82(2) . . ? O2B C1B C2B 101.5(16) . . ? O2B C1B C4B 49.7(13) . . ? C2B C1B C4B 80.6(13) . . ? C3B C2B C1B 99.8(15) . . ? C2B C3B C4B 98.4(15) . . ? O2B C4B C3B 101.0(17) . . ? O2B C4B C1B 47.9(12) . . ? C3B C4B C1B 81.2(12) . . ? 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 O4 C4 C5 C6 -169.5(4) . . . . ? O3 C4 C5 C6 9.0(6) . . . . ? O4 C4 C5 C7 3.9(7) . . . . ? O3 C4 C5 C7 -177.6(3) . . . . ? C4 C5 C6 O6 164.3(5) . . . . ? C7 C5 C6 O6 -9.2(7) . . . . ? C4 C5 C6 O1 -10.0(6) . . . . ? C7 C5 C6 O1 176.5(4) . . . . ? C17 N2 C7 N1 -10.9(5) . . . . ? C18 N2 C7 N1 165.2(3) . . . . ? C17 N2 C7 C5 170.5(4) . . . . ? C18 N2 C7 C5 -13.4(5) . . . . ? C8 N1 C7 N2 165.3(3) . . . . ? C8 N1 C7 C5 -16.1(5) . . . . ? C6 C5 C7 N2 117.5(4) . . . . ? C4 C5 C7 N2 -56.1(5) . . . . ? C6 C5 C7 N1 -61.0(5) . . . . ? C4 C5 C7 N1 125.4(4) . . . . ? C7 N1 C8 C9 117.4(4) . . . . ? C7 N1 C8 C13 -67.4(5) . . . . ? C13 C8 C9 C10 2.4(6) . . . . ? N1 C8 C9 C10 177.5(4) . . . . ? C13 C8 C9 C14 -176.1(4) . . . . ? N1 C8 C9 C14 -0.9(6) . . . . ? C8 C9 C10 C11 0.9(7) . . . . ? C14 C9 C10 C11 179.4(5) . . . . ? C9 C10 C11 C12 -3.2(7) . . . . ? C9 C10 C11 C15 177.2(5) . . . . ? C10 C11 C12 C13 2.4(7) . . . . ? C15 C11 C12 C13 -178.0(5) . . . . ? C11 C12 C13 C8 0.7(7) . . . . ? C11 C12 C13 C16 -178.7(4) . . . . ? C9 C8 C13 C12 -3.2(6) . . . . ? N1 C8 C13 C12 -178.3(4) . . . . ? C9 C8 C13 C16 176.2(4) . . . . ? N1 C8 C13 C16 1.1(6) . . . . ? O6 C6 O1 C2 164.8(4) . . . . ? C5 C6 O1 C2 -20.2(6) . . . . ? O3 C2 O1 C6 48.3(5) . . . . ? C21 C2 O1 C6 -73.4(5) . . . . ? C22 C2 O1 C6 162.7(4) . . . . ? O4 C4 O3 C2 -159.3(4) . . . . ? C5 C4 O3 C2 22.0(5) . . . . ? O1 C2 O3 C4 -49.5(5) . . . . ? C21 C2 O3 C4 73.0(5) . . . . ? C22 C2 O3 C4 -163.9(4) . . . . ? C4A O2A C1A C2A 27(3) . . . . ? O2A C1A C2A C3A -21(2) . . . . ? C1A C2A C3A C4A 10(3) . . . . ? C2A C3A C4A O2A 6(3) . . . . ? C1A O2A C4A C3A -22(4) . . . . ? C4B O2B C1B C2B -67(3) . . . . ? O2B C1B C2B C3B 45(4) . . . . ? C4B C1B C2B C3B 0(3) . . . . ? C1B C2B C3B C4B 1(4) . . . . ? C1B O2B C4B C3B 67(3) . . . . ? C2B C3B C4B O2B -44(4) . . . . ? C2B C3B C4B C1B 0(3) . . . . ? C2B C1B C4B O2B 114(3) . . . . ? O2B C1B C4B C3B -114(3) . . . . ? C2B C1B C4B C3B 0(3) . . . . ? #===END # Compound (19).H2O # CIF produced by WinGX routine CIF_UPDATE # Created on 2001-08-06 at 13:34:22 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : cw2169 dreduc struct psi_scan data_cw2169 _database_code_CSD 177784 _audit_creation_date 2001-08-06T13:34:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H50 N2 O4' _chemical_formula_structural 'C15 H50 N2 O4' _chemical_formula_sum 'C15 H28 N2 O5' _chemical_formula_weight 316.39 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'C m c 21' _symmetry_space_group_name_Hall 'C 2c -2' _symmetry_Int_Tables_number 36 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, 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' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 9.2822(5) _cell_length_b 16.716(2) _cell_length_c 11.704(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1816.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_factor_muR 0.041 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 6 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9501 _exptl_absorpt_correction_T_max 0.9581 _exptl_absorpt_correction_T_ave 0.9434 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.13247E-1 _diffrn_orient_matrix_ub_12 0.53414E-1 _diffrn_orient_matrix_ub_13 0.03695 _diffrn_orient_matrix_ub_21 -0.73418E-1 _diffrn_orient_matrix_ub_22 0.14395E-1 _diffrn_orient_matrix_ub_23 -0.59074E-1 _diffrn_orient_matrix_ub_31 -0.77726E-1 _diffrn_orient_matrix_ub_32 -0.22726E-1 _diffrn_orient_matrix_ub_33 0.49486E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 2 _diffrn_standards_decay_corr_max 1.014 _diffrn_standards_decay_corr_min 0.991 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -8 -4 -4 -2 -4 -4 -2 2 _diffrn_reflns_number 1189 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_unetI/netI 0.0165 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 984 _reflns_number_gt 855 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0571P)^2^+0.2213P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0146(16) _refine_ls_number_reflns 984 _refine_ls_number_parameters 142 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(17) _refine_diff_density_max 0.127 _refine_diff_density_min -0.117 _refine_diff_density_rms 0.028 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C 1 0.7903(2) 0.6545(3) 0.0488(8) Uani 1 2 d S . . C5 C 1 0.75336(17) 0.8794(3) 0.0402(7) Uani 1 2 d S . . C6 C 0.8682(2) 0.77272(13) 0.82891(19) 0.0455(6) Uani 1 1 d . . . C7 C 1 0.72866(17) 1.0014(3) 0.0412(7) Uani 1 2 d S . . C8 C 1 0.57689(19) 0.9676(3) 0.0513(8) Uani 1 2 d S . . C9 C 0.8666(3) 0.56983(17) 0.8935(3) 0.0738(8) Uani 1 1 d . . . H9A H 0.7822 0.5749 0.9404 0.111 Uiso 1 1 calc R . . H9B H 0.8661 0.5187 0.8562 0.111 Uiso 1 1 calc R . . H9C H 0.8671 0.6115 0.8371 0.111 Uiso 1 1 calc R . . C10 C 1 0.5119(2) 1.0584(5) 0.0913(14) Uani 1 2 d S . . H10A H 1.0842 0.5174 1.1055 0.137 Uiso 0.5 1 calc PR . . H10B H 1.0006 0.4604 1.0223 0.137 Uiso 1 2 calc SR . . H10C H 0.9153 0.517 1.1049 0.137 Uiso 0.5 1 calc PR . . C11 C 1 0.87020(19) 1.0916(3) 0.0561(9) Uani 1 2 d S . . C12 C 0.8526(7) 0.8958(5) 1.0907(10) 0.094(2) Uani 0.5 1 d P . . H12A H 0.7983 0.8702 1.1502 0.141 Uiso 0.5 1 d PR . . H12B H 0.813 0.8814 1.0177 0.141 Uiso 0.5 1 d PR . . H12C H 0.8478 0.9527 1.1001 0.141 Uiso 0.5 1 d PR . . C13 C 1.0725(12) 0.8898(5) 1.2047(8) 0.144(5) Uani 0.5 1 d P . . H13A H 1.1707 0.8718 1.2054 0.216 Uiso 0.5 1 d PR . . H13B H 1.0205 0.8645 1.2658 0.216 Uiso 0.5 1 d PR . . H13C H 1.0699 0.9468 1.2147 0.216 Uiso 0.5 1 d PR . . C14 C 1.0838(10) 0.9112(4) 0.9951(9) 0.111(3) Uani 0.5 1 d P . . H14A H 1.1818 0.8932 1.0008 0.167 Uiso 0.5 1 d PR . . H14B H 1.0805 0.9682 1.004 0.167 Uiso 0.5 1 d PR . . H14C H 1.0458 0.8969 0.9216 0.167 Uiso 0.5 1 d PR . . C21 C 1 0.7069(2) 0.6077(3) 0.0638(10) Uani 1 2 d S . . H21A H 0.9146 0.6987 0.563 0.096 Uiso 0.5 1 calc PR . . H21B H 1.002 0.6693 0.6697 0.096 Uiso 1 2 calc SR . . H21C H 1.0834 0.6994 0.5604 0.096 Uiso 0.5 1 calc PR . . C22 C 1 0.8512(3) 0.5600(4) 0.0774(12) Uani 1 2 d S . . H22A H 0.9162 0.8438 0.5131 0.116 Uiso 0.5 1 calc PR . . H22B H 1.0851 0.8447 0.5143 0.116 Uiso 0.5 1 calc PR . . H22C H 0.9987 0.904 0.5922 0.116 Uiso 1 2 calc SR . . N1 N 1 0.65340(16) 1.0338(3) 0.0557(7) Uani 1 2 d S . . N2 N 1 0.78118(18) 1.0847(3) 0.0718(10) Uani 1 2 d S . . O1 O 0.87328(15) 0.80369(10) 0.72082(13) 0.0557(5) Uani 1 1 d . . . O2 O 1 0.6640(2) 0.2808(2) 0.0730(9) Uani 1 2 d S . . O6 O 0.74822(16) 0.76724(11) 0.87306(17) 0.0652(6) Uani 1 1 d . . . H1 H 1 0.644(2) 1.107(4) 0.059(11) Uiso 1 2 d S . . H2 H 1 0.759(2) 1.153(5) 0.074(12) Uiso 1 2 d S . . H11 H 0.933(4) 0.682(2) 0.309(4) 0.093(12) Uiso 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 C2 0.0415(15) 0.0604(19) 0.0445(17) 0.0109(16) 0 0 C5 0.0382(15) 0.0391(13) 0.0435(16) 0.0040(14) 0 0 C6 0.0357(12) 0.0536(11) 0.0472(13) 0.0038(10) 0.0018(9) 0.0038(9) C7 0.0392(14) 0.0426(15) 0.0419(16) 0.0007(14) 0 0 C8 0.0557(18) 0.0452(16) 0.0529(19) 0.0047(15) 0 0 C9 0.0641(17) 0.0650(14) 0.092(2) -0.0042(15) -0.0077(16) -0.0066(11) C10 0.141(4) 0.050(2) 0.083(3) 0.017(2) 0 0 C11 0.0588(19) 0.0460(17) 0.064(2) -0.0106(16) 0 0 C12 0.063(3) 0.094(5) 0.125(7) -0.024(5) -0.002(4) 0.005(3) C13 0.221(13) 0.082(4) 0.128(7) -0.048(5) -0.106(8) 0.034(5) C14 0.131(6) 0.051(3) 0.151(8) -0.027(4) 0.061(7) -0.028(3) C21 0.072(2) 0.072(2) 0.0480(19) -0.0047(18) 0 0 C22 0.091(3) 0.080(2) 0.061(2) 0.025(2) 0 0 N1 0.082(2) 0.0456(14) 0.0397(16) 0.0053(13) 0 0 N2 0.122(3) 0.0483(16) 0.0451(19) -0.0002(14) 0 0 O1 0.0445(9) 0.0726(10) 0.0501(9) 0.0121(9) -0.0005(8) 0.0151(6) O2 0.0463(15) 0.120(3) 0.0524(14) -0.0166(17) 0 0 O6 0.0345(7) 0.0980(14) 0.0631(10) 0.0111(11) 0.0051(8) 0.0078(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 O1 1.427(3) 3_755 ? C2 O1 1.427(3) . ? C2 C21 1.498(5) . ? C2 C22 1.503(5) . ? C5 C6 1.397(2) . ? C5 C6 1.397(2) 3_755 ? C5 C7 1.486(5) . ? C6 O6 1.231(2) . ? C6 O1 1.368(3) . ? C7 N2 1.312(4) . ? C7 N1 1.314(4) . ? C8 N1 1.496(5) . ? C8 C9 1.516(4) . ? C8 C9 1.516(4) 3_755 ? C8 C10 1.520(5) . ? C11 C12 1.434(6) 3_755 ? C11 C12 1.434(6) . ? C11 N2 1.490(4) . ? C11 C13 1.521(8) 3_755 ? C11 C13 1.521(8) . ? C11 C14 1.533(9) . ? C11 C14 1.533(9) 3_755 ? C12 C14 1.291(12) 3_755 ? C12 C13 1.509(15) 3_755 ? C13 C13 1.35(2) 3_755 ? C13 C12 1.509(15) 3_755 ? C14 C12 1.291(12) 3_755 ? C14 C14 1.556(18) 3_755 ? 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 O1 C2 O1 111.1(3) 3_755 . ? O1 C2 C21 110.16(18) 3_755 . ? O1 C2 C21 110.16(18) . . ? O1 C2 C22 107.12(17) 3_755 . ? O1 C2 C22 107.12(17) . . ? C21 C2 C22 111.1(3) . . ? C6 C5 C6 122.3(3) . 3_755 ? C6 C5 C7 118.10(14) . . ? C6 C5 C7 118.10(14) 3_755 . ? O6 C6 O1 116.59(19) . . ? O6 C6 C5 126.7(2) . . ? O1 C6 C5 116.68(19) . . ? N2 C7 N1 115.2(3) . . ? N2 C7 C5 121.9(3) . . ? N1 C7 C5 122.9(3) . . ? N1 C8 C9 111.28(19) . . ? N1 C8 C9 111.28(19) . 3_755 ? C9 C8 C9 109.5(3) . 3_755 ? N1 C8 C10 104.4(3) . . ? C9 C8 C10 110.1(2) . . ? C9 C8 C10 110.1(2) 3_755 . ? C12 C11 C12 145.3(6) 3_755 . ? C12 C11 N2 107.3(3) 3_755 . ? C12 C11 N2 107.3(3) . . ? C12 C11 C13 111.4(7) 3_755 3_755 ? C12 C11 C13 61.3(6) . 3_755 ? N2 C11 C13 105.2(4) . 3_755 ? C12 C11 C13 61.3(6) 3_755 . ? C12 C11 C13 111.4(7) . . ? N2 C11 C13 105.2(4) . . ? C13 C11 C13 52.5(10) 3_755 . ? C12 C11 C14 51.5(5) 3_755 . ? C12 C11 C14 110.2(7) . . ? N2 C11 C14 114.0(3) . . ? C13 C11 C14 140.3(5) 3_755 . ? C13 C11 C14 108.7(6) . . ? C12 C11 C14 110.2(7) 3_755 3_755 ? C12 C11 C14 51.5(5) . 3_755 ? N2 C11 C14 114.0(3) . 3_755 ? C13 C11 C14 108.7(6) 3_755 3_755 ? C13 C11 C14 140.3(5) . 3_755 ? C14 C11 C14 61.0(8) . 3_755 ? C14 C12 C11 68.2(5) 3_755 . ? C14 C12 C13 124.7(7) 3_755 3_755 ? C11 C12 C13 62.2(5) . 3_755 ? C13 C13 C12 117.5(5) 3_755 3_755 ? C13 C13 C11 63.8(5) 3_755 . ? C12 C13 C11 56.5(4) 3_755 . ? C12 C14 C11 60.3(5) 3_755 . ? C12 C14 C14 117.2(5) 3_755 3_755 ? C11 C14 C14 59.5(4) . 3_755 ? C7 N1 C8 132.0(3) . . ? C7 N2 C11 135.1(3) . . ? C6 O1 C2 118.18(17) . . ? 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 C5 C6 O6 -170.22(18) 3_755 . . . ? C7 C5 C6 O6 -4.5(4) . . . . ? C6 C5 C6 O1 7.2(4) 3_755 . . . ? C7 C5 C6 O1 172.9(2) . . . . ? C6 C5 C7 N2 -83.2(2) . . . . ? C6 C5 C7 N2 83.2(2) 3_755 . . . ? C6 C5 C7 N1 96.8(2) . . . . ? C6 C5 C7 N1 -96.8(2) 3_755 . . . ? C12 C11 C12 C14 68.0(17) 3_755 . . 3_755 ? N2 C11 C12 C14 -107.2(5) . . . 3_755 ? C13 C11 C12 C14 154.6(7) 3_755 . . 3_755 ? C13 C11 C12 C14 138.2(7) . . . 3_755 ? C14 C11 C12 C14 17.4(5) . . . 3_755 ? C12 C11 C12 C13 -86.6(17) 3_755 . . 3_755 ? N2 C11 C12 C13 98.2(5) . . . 3_755 ? C13 C11 C12 C13 -16.4(5) . . . 3_755 ? C14 C11 C12 C13 -137.2(6) . . . 3_755 ? C14 C11 C12 C13 -154.6(7) 3_755 . . 3_755 ? C12 C11 C13 C13 160.6(4) 3_755 . . 3_755 ? C12 C11 C13 C13 18.2(4) . . . 3_755 ? N2 C11 C13 C13 -97.7(3) . . . 3_755 ? C14 C11 C13 C13 139.9(4) . . . 3_755 ? C14 C11 C13 C13 73.0(10) 3_755 . . 3_755 ? C12 C11 C13 C12 -142.4(8) . . . 3_755 ? N2 C11 C13 C12 101.7(4) . . . 3_755 ? C13 C11 C13 C12 -160.6(4) 3_755 . . 3_755 ? C14 C11 C13 C12 -20.8(6) . . . 3_755 ? C14 C11 C13 C12 -87.6(11) 3_755 . . 3_755 ? C12 C11 C14 C12 145.8(8) . . . 3_755 ? N2 C11 C14 C12 -93.5(5) . . . 3_755 ? C13 C11 C14 C12 76.7(12) 3_755 . . 3_755 ? C13 C11 C14 C12 23.4(6) . . . 3_755 ? C14 C11 C14 C12 161.3(4) 3_755 . . 3_755 ? C12 C11 C14 C14 -161.3(4) 3_755 . . 3_755 ? C12 C11 C14 C14 -15.5(4) . . . 3_755 ? N2 C11 C14 C14 105.2(3) . . . 3_755 ? C13 C11 C14 C14 -84.6(10) 3_755 . . 3_755 ? C13 C11 C14 C14 -137.8(5) . . . 3_755 ? N2 C7 N1 C8 180.000(2) . . . . ? C5 C7 N1 C8 0.000(2) . . . . ? C9 C8 N1 C7 -61.2(2) . . . . ? C9 C8 N1 C7 61.2(2) 3_755 . . . ? C10 C8 N1 C7 180.000(2) . . . . ? N1 C7 N2 C11 180.000(2) . . . . ? C5 C7 N2 C11 0.000(3) . . . . ? C12 C11 N2 C7 -88.6(5) 3_755 . . . ? C12 C11 N2 C7 88.6(5) . . . . ? C13 C11 N2 C7 152.7(5) 3_755 . . . ? C13 C11 N2 C7 -152.7(5) . . . . ? C14 C11 N2 C7 -33.7(5) . . . . ? C14 C11 N2 C7 33.7(5) 3_755 . . . ? O6 C6 O1 C2 -162.3(2) . . . . ? C5 C6 O1 C2 20.0(3) . . . . ? O1 C2 O1 C6 -44.6(3) 3_755 . . . ? C21 C2 O1 C6 77.7(3) . . . . ? C22 C2 O1 C6 -161.3(3) . . . . ? #===END