# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_section_title ;Crystal structures and characterization of the polymorphs of (2-furyl)oxoacetamide ; _publ_contact_author_name 'Prof. Joel Bernstein' _publ_contact_author_email YOEL@BGU.AC.IL loop_ _publ_author_name I.Barsky J.Bernstein # Attachment 'Form_I.cif' data_2ffo11 _database_code_depnum_ccdc_archive 'CCDC 659328' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 N O3' _chemical_formula_weight 139.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 39.698(16) _cell_length_b 48.359(19) _cell_length_c 3.8476(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7386(5) _cell_formula_units_Z 48 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3456 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10577 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.1090 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -60 _diffrn_reflns_limit_k_max 63 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 28.39 _reflns_number_total 3714 _reflns_number_gt 1781 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0181P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.8(11) _refine_ls_number_reflns 3714 _refine_ls_number_parameters 331 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0513 _refine_ls_goodness_of_fit_ref 0.813 _refine_ls_restrained_S_all 0.813 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.13551(7) 0.00796(6) -0.0096(9) 0.0503(9) Uani 1 1 d . . . C2 C 0.15327(8) 0.02646(6) 0.1705(9) 0.0522(9) Uani 1 1 d . . . C3 C 0.13323(7) 0.05007(6) 0.1950(9) 0.0457(8) Uani 1 1 d . . . C4 C 0.10407(6) 0.04473(5) 0.0260(8) 0.0374(7) Uani 1 1 d . . . C5 C 0.07370(7) 0.06008(5) -0.0572(9) 0.0441(8) Uani 1 1 d . . . C6 C 0.07129(8) 0.08954(5) 0.0877(9) 0.0502(9) Uani 1 1 d . . . C7 C 0.20954(7) 0.12375(6) 0.8170(9) 0.0529(9) Uani 1 1 d . . . C8 C 0.18749(7) 0.10366(6) 0.8720(8) 0.0486(9) Uani 1 1 d . . . C9 C 0.20269(7) 0.07936(6) 0.7457(8) 0.0427(8) Uani 1 1 d . . . C10 C 0.23304(6) 0.08623(5) 0.6149(8) 0.0374(7) Uani 1 1 d . . . C11 C 0.25998(6) 0.07213(5) 0.4357(8) 0.0376(7) Uani 1 1 d . . . C12 C 0.25676(6) 0.04087(5) 0.3769(8) 0.0372(7) Uani 1 1 d . . . C13 C 0.47568(8) 0.03898(7) 0.7172(11) 0.0697(11) Uani 1 1 d . . . C14 C 0.45834(8) 0.01978(7) 0.8860(10) 0.0643(11) Uani 1 1 d . . . C15 C 0.42539(7) 0.03024(6) 0.9137(8) 0.0493(9) Uani 1 1 d . . . C16 C 0.42480(6) 0.05508(5) 0.7615(8) 0.0406(7) Uani 1 1 d . . . C17 C 0.39923(6) 0.07585(5) 0.6954(8) 0.0413(8) Uani 1 1 d . . . C18 C 0.36427(6) 0.07185(5) 0.8614(7) 0.0407(8) Uani 1 1 d . . . H1 H 0.1390(5) -0.0111(4) -0.078(7) 0.058(9) Uiso 1 1 d . . . H2 H 0.1734(5) 0.0241(4) 0.265(7) 0.043(8) Uiso 1 1 d . . . H3 H 0.1379(4) 0.0673(3) 0.291(6) 0.024(6) Uiso 1 1 d . . . H4 H 0.0383(7) 0.1156(5) 0.066(10) 0.086(15) Uiso 1 1 d . . . H5 H 0.0276(9) 0.0888(7) -0.116(13) 0.17(2) Uiso 1 1 d . . . H6 H 0.2097(5) 0.1437(5) 0.858(8) 0.071(9) Uiso 1 1 d . . . H7 H 0.1667(5) 0.1069(4) 0.970(8) 0.057(9) Uiso 1 1 d . . . H8 H 0.1936(5) 0.0626(4) 0.750(7) 0.056(9) Uiso 1 1 d . . . H9 H 0.2834(5) 0.0110(4) 0.150(7) 0.050(9) Uiso 1 1 d . . . H10 H 0.3008(6) 0.0402(5) 0.187(10) 0.102(13) Uiso 1 1 d . . . H11 H 0.4978(6) 0.0401(4) 0.638(8) 0.069(10) Uiso 1 1 d . . . H12 H 0.4666(6) 0.0031(4) 0.958(8) 0.065(10) Uiso 1 1 d . . . H13 H 0.4094(4) 0.0218(3) 1.012(6) 0.018(7) Uiso 1 1 d . . . H14 H 0.3267(7) 0.0931(5) 0.927(10) 0.103(15) Uiso 1 1 d . . . H15 H 0.3531(5) 0.1101(4) 0.728(7) 0.061(9) Uiso 1 1 d . . . N1 N 0.04207(8) 0.10156(7) -0.0017(9) 0.0775(11) Uani 1 1 d . . . N2 N 0.28318(6) 0.02968(5) 0.2219(8) 0.0539(8) Uani 1 1 d . . . N3 N 0.34514(7) 0.09410(5) 0.8389(8) 0.0547(8) Uani 1 1 d . . . O1 O 0.10510(4) 0.01822(3) -0.1023(5) 0.0492(6) Uani 1 1 d . . . O2 O 0.05064(4) 0.05069(3) -0.2327(6) 0.0627(7) Uani 1 1 d . . . O3 O 0.09353(5) 0.10003(4) 0.2596(6) 0.0771(7) Uani 1 1 d . . . O4 O 0.23784(4) 0.11423(3) 0.6557(5) 0.0531(6) Uani 1 1 d . . . O5 O 0.28457(4) 0.08448(3) 0.3208(6) 0.0538(6) Uani 1 1 d . . . O6 O 0.23139(4) 0.02846(3) 0.4700(6) 0.0520(6) Uani 1 1 d . . . O7 O 0.45650(4) 0.06118(3) 0.6318(6) 0.0609(6) Uani 1 1 d . . . O8 O 0.40435(4) 0.09623(3) 0.5169(6) 0.0590(6) Uani 1 1 d . . . O9 O 0.35576(4) 0.05035(3) 1.0025(5) 0.0555(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0461(19) 0.043(2) 0.061(3) 0.0049(18) 0.0070(19) 0.0065(17) C2 0.0381(19) 0.065(2) 0.053(3) 0.008(2) -0.0040(19) 0.0014(18) C3 0.0524(19) 0.0372(18) 0.047(2) -0.0073(17) 0.0017(17) -0.0071(16) C4 0.0440(17) 0.0315(16) 0.037(2) -0.0035(14) 0.0049(16) -0.0039(13) C5 0.0473(17) 0.0364(17) 0.049(2) -0.0049(17) 0.0040(18) -0.0018(15) C6 0.064(2) 0.0375(18) 0.049(3) 0.0005(16) 0.0140(19) 0.0011(16) C7 0.057(2) 0.0397(19) 0.062(3) -0.0030(19) 0.0058(18) 0.0105(17) C8 0.048(2) 0.049(2) 0.049(2) -0.0048(18) 0.0114(18) 0.0077(17) C9 0.0453(18) 0.0418(19) 0.041(2) -0.0031(16) 0.0034(17) -0.0048(15) C10 0.0375(16) 0.0336(16) 0.041(2) 0.0004(15) -0.0040(16) -0.0012(13) C11 0.0342(15) 0.0389(16) 0.040(2) 0.0014(15) -0.0080(16) -0.0042(13) C12 0.0374(16) 0.0346(16) 0.040(2) 0.0077(15) -0.0104(16) -0.0020(14) C13 0.040(2) 0.081(3) 0.088(3) 0.002(2) 0.008(2) 0.012(2) C14 0.060(2) 0.067(2) 0.066(3) 0.013(2) 0.000(2) 0.017(2) C15 0.049(2) 0.052(2) 0.047(2) 0.0107(19) 0.0106(18) -0.0034(17) C16 0.0341(16) 0.0441(17) 0.044(2) 0.0026(15) 0.0089(16) -0.0050(14) C17 0.0412(17) 0.0433(17) 0.039(2) 0.0045(15) 0.0027(16) -0.0127(14) C18 0.0439(17) 0.0374(17) 0.041(2) 0.0042(15) -0.0009(16) -0.0051(14) N1 0.078(2) 0.061(2) 0.094(3) -0.013(2) 0.001(2) 0.031(2) N2 0.0454(16) 0.0386(16) 0.078(2) -0.0096(16) 0.0135(16) 0.0024(14) N3 0.0492(18) 0.0453(18) 0.069(2) 0.0180(16) 0.0061(17) 0.0026(15) O1 0.0429(11) 0.0383(11) 0.0665(17) -0.0095(11) -0.0033(11) 0.0029(9) O2 0.0471(11) 0.0606(12) 0.080(2) -0.0149(13) -0.0125(13) 0.0005(10) O3 0.0850(15) 0.0495(13) 0.097(2) -0.0292(13) -0.0070(17) -0.0006(11) O4 0.0509(11) 0.0364(11) 0.0721(18) -0.0007(11) 0.0090(13) 0.0016(9) O5 0.0399(10) 0.0435(11) 0.0782(19) 0.0010(11) 0.0151(12) -0.0063(9) O6 0.0404(10) 0.0407(11) 0.0748(16) 0.0019(11) 0.0047(12) -0.0064(9) O7 0.0434(11) 0.0587(12) 0.0806(18) 0.0047(13) 0.0118(13) -0.0020(10) O8 0.0583(12) 0.0487(12) 0.0701(17) 0.0231(12) 0.0092(12) -0.0069(10) O9 0.0505(11) 0.0417(11) 0.0743(18) 0.0182(12) 0.0175(12) 0.0000(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.333(4) . ? C1 O1 1.353(3) . ? C2 C3 1.394(3) . ? C3 C4 1.353(3) . ? C4 O1 1.374(3) . ? C4 C5 1.452(3) . ? C5 O2 1.225(3) . ? C5 C6 1.533(3) . ? C6 O3 1.215(3) . ? C6 N1 1.342(4) . ? C7 C8 1.325(4) . ? C7 O4 1.363(3) . ? C8 C9 1.407(3) . ? C9 C10 1.347(3) . ? C10 O4 1.376(3) . ? C10 C11 1.444(3) . ? C11 O5 1.227(2) . ? C11 C12 1.534(3) . ? C12 O6 1.226(3) . ? C12 N2 1.322(3) . ? C13 C14 1.326(4) . ? C13 O7 1.356(3) . ? C14 C15 1.407(4) . ? C15 C16 1.337(3) . ? C16 O7 1.385(3) . ? C16 C17 1.451(3) . ? C17 O8 1.218(3) . ? C17 C18 1.540(3) . ? C18 O9 1.220(3) . ? C18 N3 1.320(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 C2 C1 O1 111.3(3) . . ? C1 C2 C3 106.5(3) . . ? C4 C3 C2 107.4(3) . . ? C3 C4 O1 109.0(2) . . ? C3 C4 C5 136.0(2) . . ? O1 C4 C5 115.0(2) . . ? O2 C5 C4 123.6(2) . . ? O2 C5 C6 119.9(3) . . ? C4 C5 C6 116.6(3) . . ? O3 C6 N1 125.9(3) . . ? O3 C6 C5 122.8(3) . . ? N1 C6 C5 111.3(3) . . ? C8 C7 O4 111.7(3) . . ? C7 C8 C9 105.9(3) . . ? C10 C9 C8 107.8(3) . . ? C9 C10 O4 108.9(2) . . ? C9 C10 C11 136.4(3) . . ? O4 C10 C11 114.6(2) . . ? O5 C11 C10 122.1(2) . . ? O5 C11 C12 119.5(2) . . ? C10 C11 C12 118.3(2) . . ? O6 C12 N2 125.7(2) . . ? O6 C12 C11 120.5(2) . . ? N2 C12 C11 113.8(2) . . ? C14 C13 O7 112.4(3) . . ? C13 C14 C15 105.5(3) . . ? C16 C15 C14 107.8(3) . . ? C15 C16 O7 109.5(2) . . ? C15 C16 C17 135.3(3) . . ? O7 C16 C17 115.2(2) . . ? O8 C17 C16 122.8(2) . . ? O8 C17 C18 119.1(2) . . ? C16 C17 C18 118.1(2) . . ? O9 C18 N3 124.4(3) . . ? O9 C18 C17 122.7(2) . . ? N3 C18 C17 112.9(3) . . ? C1 O1 C4 105.9(2) . . ? C7 O4 C10 105.6(2) . . ? C13 O7 C16 104.7(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 O1 C1 C2 C3 -0.1(4) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 O1 0.5(3) . . . . ? C2 C3 C4 C5 -177.2(3) . . . . ? C3 C4 C5 O2 176.5(3) . . . . ? O1 C4 C5 O2 -1.1(4) . . . . ? C3 C4 C5 C6 -3.6(5) . . . . ? O1 C4 C5 C6 178.8(2) . . . . ? O2 C5 C6 O3 -179.1(3) . . . . ? C4 C5 C6 O3 1.0(4) . . . . ? O2 C5 C6 N1 0.7(4) . . . . ? C4 C5 C6 N1 -179.2(3) . . . . ? O4 C7 C8 C9 1.4(4) . . . . ? C7 C8 C9 C10 -1.1(4) . . . . ? C8 C9 C10 O4 0.4(3) . . . . ? C8 C9 C10 C11 -176.2(3) . . . . ? C9 C10 C11 O5 174.4(3) . . . . ? O4 C10 C11 O5 -2.1(4) . . . . ? C9 C10 C11 C12 -3.3(5) . . . . ? O4 C10 C11 C12 -179.8(2) . . . . ? O5 C11 C12 O6 -175.3(3) . . . . ? C10 C11 C12 O6 2.4(4) . . . . ? O5 C11 C12 N2 4.6(4) . . . . ? C10 C11 C12 N2 -177.7(3) . . . . ? O7 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 O7 0.4(4) . . . . ? C14 C15 C16 C17 178.3(3) . . . . ? C15 C16 C17 O8 -172.4(3) . . . . ? O7 C16 C17 O8 5.3(4) . . . . ? C15 C16 C17 C18 8.0(5) . . . . ? O7 C16 C17 C18 -174.3(2) . . . . ? O8 C17 C18 O9 169.6(3) . . . . ? C16 C17 C18 O9 -10.8(4) . . . . ? O8 C17 C18 N3 -11.4(4) . . . . ? C16 C17 C18 N3 168.2(3) . . . . ? C2 C1 O1 C4 0.4(3) . . . . ? C3 C4 O1 C1 -0.5(3) . . . . ? C5 C4 O1 C1 177.7(2) . . . . ? C8 C7 O4 C10 -1.2(3) . . . . ? C9 C10 O4 C7 0.4(3) . . . . ? C11 C10 O4 C7 177.9(2) . . . . ? C14 C13 O7 C16 0.4(4) . . . . ? C15 C16 O7 C13 -0.5(3) . . . . ? C17 C16 O7 C13 -178.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.146 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.033 # Attachment 'Form_II.cif' data_2ff2f1 _database_code_depnum_ccdc_archive 'CCDC 659329' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 N O3' _chemical_formula_weight 139.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.7455(19) _cell_length_b 7.257(4) _cell_length_c 11.424(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.881(9) _cell_angle_gamma 90.00 _cell_volume 308.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 144 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1937 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.14 _reflns_number_total 1005 _reflns_number_gt 712 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _refine_ls_number_reflns 1005 _refine_ls_number_parameters 111 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1345 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2114(11) 0.1290(6) 0.0696(4) 0.0551(10) Uani 1 1 d . . . C2 C 0.0735(11) 0.0490(6) 0.1612(3) 0.0545(10) Uani 1 1 d . . . C3 C 0.0953(10) 0.1834(5) 0.2530(3) 0.0489(9) Uani 1 1 d . . . C4 C 0.2481(8) 0.3366(4) 0.2104(3) 0.0391(8) Uani 1 1 d . . . C5 C 0.3443(8) 0.5187(5) 0.2549(3) 0.0402(8) Uani 1 1 d . . . C6 C 0.2202(9) 0.5764(5) 0.3746(3) 0.0425(8) Uani 1 1 d . . . H1 H 0.214(10) 0.101(6) -0.011(3) 0.059(12) Uiso 1 1 d . . . H2 H -0.012(10) -0.069(7) 0.173(3) 0.058(11) Uiso 1 1 d . . . H3 H 0.062(10) 0.157(6) 0.334(3) 0.053(11) Uiso 1 1 d . . . H4 H 0.264(13) 0.794(8) 0.467(4) 0.076(15) Uiso 1 1 d . . . H5 H 0.470(17) 0.817(10) 0.363(5) 0.12(2) Uiso 1 1 d . . . N1 N 0.3048(10) 0.7508(5) 0.4004(3) 0.0582(10) Uani 1 1 d . . . O1 O 0.3203(7) 0.3042(3) 0.0962(2) 0.0510(7) Uani 1 1 d . . . O2 O 0.5166(7) 0.6285(4) 0.2016(2) 0.0554(7) Uani 1 1 d . . . O3 O 0.0522(8) 0.4750(4) 0.4332(2) 0.0624(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.072(3) 0.045(2) 0.048(2) -0.0088(17) 0.0055(18) 0.0053(19) C2 0.059(2) 0.037(2) 0.068(2) -0.0034(19) 0.0096(17) 0.0002(17) C3 0.051(2) 0.046(2) 0.052(2) 0.0016(17) 0.0159(16) 0.0031(17) C4 0.0423(17) 0.038(2) 0.0377(17) -0.0017(13) 0.0083(13) 0.0051(14) C5 0.0396(17) 0.0396(19) 0.0428(16) 0.0017(14) 0.0110(14) 0.0058(14) C6 0.047(2) 0.0421(19) 0.0395(17) 0.0034(15) 0.0095(14) 0.0053(14) N1 0.070(2) 0.050(2) 0.059(2) -0.0125(16) 0.0238(18) -0.0058(17) O1 0.0648(16) 0.0450(15) 0.0448(13) -0.0021(11) 0.0135(11) 0.0012(12) O2 0.0694(17) 0.0448(16) 0.0565(15) 0.0028(12) 0.0283(13) -0.0050(13) O3 0.088(2) 0.0501(17) 0.0546(14) 0.0076(12) 0.0336(14) 0.0024(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.345(6) . ? C1 O1 1.360(5) . ? C2 C3 1.428(5) . ? C3 C4 1.363(5) . ? C4 O1 1.379(4) . ? C4 C5 1.448(4) . ? C5 O2 1.225(4) . ? C5 C6 1.547(4) . ? C6 O3 1.213(4) . ? C6 N1 1.330(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 C2 C1 O1 111.1(4) . . ? C1 C2 C3 106.2(4) . . ? C4 C3 C2 106.8(3) . . ? C3 C4 O1 109.2(3) . . ? C3 C4 C5 135.8(3) . . ? O1 C4 C5 115.0(3) . . ? O2 C5 C4 122.9(3) . . ? O2 C5 C6 119.0(3) . . ? C4 C5 C6 118.1(3) . . ? O3 C6 N1 125.4(4) . . ? O3 C6 C5 122.9(3) . . ? N1 C6 C5 111.6(3) . . ? C1 O1 C4 106.7(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 O1 C1 C2 C3 0.1(5) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 O1 0.3(4) . . . . ? C2 C3 C4 C5 179.5(4) . . . . ? C3 C4 C5 O2 172.2(4) . . . . ? O1 C4 C5 O2 -8.6(4) . . . . ? C3 C4 C5 C6 -8.3(5) . . . . ? O1 C4 C5 C6 170.8(3) . . . . ? O2 C5 C6 O3 -179.2(3) . . . . ? C4 C5 C6 O3 1.3(5) . . . . ? O2 C5 C6 N1 4.0(4) . . . . ? C4 C5 C6 N1 -175.5(3) . . . . ? C2 C1 O1 C4 0.1(4) . . . . ? C3 C4 O1 C1 -0.3(4) . . . . ? C5 C4 O1 C1 -179.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.14 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.189 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.057