# Copyright The Royal Society of Chemistry, 1999 # CCDC Number :182/1118 #====================================================================== data_global #====================================================================== # 1. SUBMISSION DETAILS _publ_contact_author ; Dr Jonathan P. H. Charmant, School of Chemistry, Cantocks Close, University of Bristol. Bristol. BS8 1TS. ; _publ_contact_author_phone '0117 928 9812' _publ_contact_author_fax '0117 929 0509' _publ_contact_author_email jon.charmant@bris.ac.uk _publ_requested_journal 'Chemical Communications' _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication as a part of a paper in Chemical Communications. The name of the manuscript is: Aldehydes and Ketones as Dipolarophiles. Application to the Synthesis of Oxapenams. paper ref is 8/08688E Yours sincerely, J.P.H. Charmant. ; #====================================================================== # data_oadbya _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 F6 N2 O6' _chemical_formula_sum 'C15 H10 F6 N2 O6' _chemical_formula_weight 428.25 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.658(1) _cell_length_b 8.055(1) _cell_length_c 34.764(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3264.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 243 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.743 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.811 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details ; Based on multiple and symmetry equivalent measurements using Bruker SADABS area detector and absorption correction software. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 13916 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 23.28 _reflns_number_total 2344 _reflns_number_gt 2108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v4' _computing_cell_refinement 'Bruker SMART v4' _computing_data_reduction 'Bruker SAINT v4' _computing_structure_solution 'Bruker SHELXTL v6' _computing_structure_refinement 'Bruker SHELXTL v6' _computing_molecular_graphics 'Bruker SHELXTL v6' _computing_publication_material 'Bruker SHELXTL v6' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR nd goodness of fit S are based on F^2^, conventional R-factors R are ased on F, with F set to zero for negative F^2^. The threshold expression f F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. nd is not relevant to the choice of reflections for refinement. R-factors ased on F^2^ are statistically about twice as large as those based on F, nd 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^)+(0.0279P)^2^+1.8016P] where w=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2344 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.194 _refine_ls_restrained_S_all 1.194 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.03277(12) 1.19248(17) 0.19716(4) 0.0301(4) Uani 1 1 d . . . C2 C 0.01063(17) 1.0236(2) 0.18999(6) 0.0234(4) Uani 1 1 d . . . C3 C -0.03035(17) 1.0090(2) 0.14644(5) 0.0217(4) Uani 1 1 d . . . H3 H -0.0994(17) 0.951(2) 0.1447(5) 0.018(5) Uiso 1 1 d . . . N4 N -0.04505(13) 1.1820(2) 0.13672(4) 0.0225(4) Uani 1 1 d . . . C5 C 0.02027(18) 1.2883(2) 0.16236(6) 0.0262(5) Uani 1 1 d . . . H5 H 0.0962(18) 1.323(2) 0.1542(6) 0.022(5) Uiso 1 1 d . . . C6 C -0.07959(18) 1.4121(3) 0.16338(6) 0.0308(5) Uani 1 1 d . . . H6A H -0.1094 1.4360 0.1895 0.037 Uiso 1 1 calc R . . H6B H -0.0662 1.5152 0.1486 0.037 Uiso 1 1 calc R . . C7 C -0.14578(18) 1.2782(3) 0.14162(6) 0.0265(5) Uani 1 1 d . . . O7 O -0.24215(12) 1.25225(19) 0.13163(4) 0.0370(4) Uani 1 1 d . . . C8 C 0.05678(16) 0.9312(2) 0.11905(5) 0.0218(4) Uani 1 1 d . . . O8 O 0.14276(12) 1.00039(17) 0.10856(4) 0.0295(4) Uani 1 1 d . . . O9 O 0.02393(11) 0.78024(15) 0.10807(4) 0.0230(3) Uani 1 1 d . . . C10 C 0.10094(16) 0.6999(2) 0.08086(6) 0.0248(5) Uani 1 1 d . . . H10A H 0.1745 0.6725 0.0936 0.030 Uiso 1 1 calc R . . H10B H 0.1171 0.7754 0.0591 0.030 Uiso 1 1 calc R . . C11 C 0.04488(16) 0.5443(2) 0.06646(5) 0.0224(4) Uani 1 1 d . . . C12 C -0.07139(18) 0.5386(3) 0.05770(7) 0.0326(5) Uani 1 1 d . . . H12 H -0.1178 0.6341 0.0616 0.039 Uiso 1 1 calc R . . C13 C -0.11996(17) 0.3947(3) 0.04334(6) 0.0306(5) Uani 1 1 d . . . H13 H -0.1991 0.3903 0.0369 0.037 Uiso 1 1 calc R . . C14 C -0.05034(16) 0.2580(2) 0.03865(5) 0.0219(4) Uani 1 1 d . . . O14B O -0.18594(12) 0.11186(18) 0.00364(4) 0.0340(4) Uani 1 1 d . . . O14A O -0.06318(13) -0.02885(17) 0.03703(4) 0.0353(4) Uani 1 1 d . . . N14 N -0.10317(14) 0.1034(2) 0.02553(5) 0.0258(4) Uani 1 1 d . . . C15 C 0.06513(17) 0.2594(2) 0.04678(6) 0.0253(5) Uani 1 1 d . . . H15 H 0.1110 0.1633 0.0430 0.030 Uiso 1 1 calc R . . C16 C 0.11220(16) 0.4049(2) 0.06055(6) 0.0246(5) Uani 1 1 d . . . H16 H 0.1920 0.4096 0.0661 0.029 Uiso 1 1 calc R . . C17 C 0.11988(18) 0.9244(3) 0.19986(6) 0.0321(5) Uani 1 1 d . . . F17C F 0.11439(11) 0.77009(16) 0.18620(4) 0.0446(4) Uani 1 1 d . . . F17B F 0.13715(11) 0.91309(18) 0.23762(3) 0.0466(4) Uani 1 1 d . . . F17A F 0.21227(10) 0.99560(18) 0.18497(4) 0.0488(4) Uani 1 1 d . . . C18 C -0.08890(18) 0.9727(3) 0.21640(6) 0.0304(5) Uani 1 1 d . . . F18C F -0.10963(12) 0.81038(16) 0.21444(4) 0.0450(4) Uani 1 1 d . . . F18B F -0.18495(10) 1.05175(17) 0.20563(3) 0.0402(3) Uani 1 1 d . . . F18A F -0.07074(11) 1.01189(16) 0.25296(3) 0.0422(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0406(8) 0.0237(8) 0.0259(7) -0.0013(6) -0.0078(6) -0.0041(6) C2 0.0245(11) 0.0212(11) 0.0246(10) -0.0005(8) -0.0016(8) -0.0012(8) C3 0.0179(10) 0.0240(11) 0.0232(10) -0.0001(8) -0.0004(8) -0.0029(9) N4 0.0208(8) 0.0244(9) 0.0224(9) -0.0009(7) 0.0005(7) 0.0010(7) C5 0.0253(11) 0.0258(12) 0.0275(11) -0.0001(9) 0.0006(9) -0.0037(9) C6 0.0362(12) 0.0261(12) 0.0302(12) 0.0003(9) 0.0020(10) 0.0019(9) C7 0.0276(12) 0.0278(11) 0.0240(10) 0.0040(9) 0.0041(9) 0.0066(9) O7 0.0247(8) 0.0411(9) 0.0452(9) -0.0003(7) -0.0049(7) 0.0074(7) C8 0.0190(10) 0.0223(11) 0.0242(10) 0.0002(8) -0.0021(9) 0.0011(8) O8 0.0228(8) 0.0286(8) 0.0372(8) -0.0057(6) 0.0078(6) -0.0055(6) O9 0.0216(7) 0.0217(7) 0.0256(7) -0.0042(6) 0.0045(6) -0.0015(6) C10 0.0208(10) 0.0249(11) 0.0287(11) -0.0056(9) 0.0041(8) 0.0008(8) C11 0.0224(11) 0.0241(11) 0.0206(10) 0.0002(8) 0.0014(8) -0.0002(8) C12 0.0246(11) 0.0245(11) 0.0488(14) -0.0051(10) -0.0060(10) 0.0068(9) C13 0.0205(11) 0.0288(12) 0.0424(13) 0.0002(10) -0.0085(9) 0.0007(9) C14 0.0249(10) 0.0219(10) 0.0191(10) -0.0008(8) -0.0009(8) -0.0026(8) O14B 0.0285(8) 0.0385(9) 0.0348(8) -0.0023(7) -0.0076(7) -0.0082(7) O14A 0.0396(9) 0.0228(8) 0.0436(9) 0.0004(7) -0.0035(7) -0.0010(7) N14 0.0247(9) 0.0272(10) 0.0255(9) -0.0018(8) 0.0014(8) -0.0033(8) C15 0.0229(10) 0.0232(11) 0.0298(11) -0.0031(9) 0.0003(9) 0.0035(9) C16 0.0175(10) 0.0283(11) 0.0279(11) -0.0026(9) 0.0013(8) 0.0010(8) C17 0.0305(12) 0.0360(13) 0.0299(12) 0.0003(10) -0.0029(10) 0.0018(10) F17C 0.0534(8) 0.0350(8) 0.0454(8) -0.0028(6) -0.0100(6) 0.0174(6) F17B 0.0459(8) 0.0656(10) 0.0282(7) 0.0015(6) -0.0132(6) 0.0138(7) F17A 0.0223(7) 0.0720(10) 0.0520(8) 0.0071(7) -0.0021(6) 0.0012(6) C18 0.0330(12) 0.0325(13) 0.0259(12) 0.0005(9) 0.0013(9) -0.0002(10) F18C 0.0535(8) 0.0369(8) 0.0445(8) 0.0046(6) 0.0090(6) -0.0144(6) F18B 0.0256(7) 0.0613(9) 0.0337(7) 0.0039(6) 0.0073(6) 0.0062(6) F18A 0.0503(8) 0.0542(9) 0.0220(7) -0.0005(6) 0.0039(6) 0.0027(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. lanes) are estimated using the full covariance matrix. The cell esds are aken into account individually in the estimation of esds in distances, ngles and torsion angles; correlations between esds in cell parameters are nly used when they are defined by crystal symmetry. An approximate isotropic) treatment of cell esds is used for estimating esds involving l.s. lanes. ; 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 C2 1.407(2) . ? O1 C5 1.442(2) . ? C2 C18 1.535(3) . ? C2 C17 1.542(3) . ? C2 C3 1.592(3) . ? C3 N4 1.444(3) . ? C3 C8 1.527(3) . ? N4 C7 1.417(3) . ? N4 C5 1.452(3) . ? C5 C6 1.533(3) . ? C6 C7 1.527(3) . ? C7 O7 1.194(2) . ? C8 O8 1.204(2) . ? C8 O9 1.331(2) . ? O9 C10 1.456(2) . ? C10 C11 1.500(3) . ? C11 C16 1.385(3) . ? C11 C12 1.390(3) . ? C12 C13 1.383(3) . ? C13 C14 1.378(3) . ? C14 C15 1.376(3) . ? C14 N14 1.462(3) . ? O14B N14 1.231(2) . ? O14A N14 1.229(2) . ? C15 C16 1.380(3) . ? C17 F17A 1.325(3) . ? C17 F17B 1.331(2) . ? C17 F17C 1.332(3) . ? C18 F18A 1.326(2) . ? C18 F18C 1.332(3) . ? C18 F18B 1.341(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 C2 O1 C5 110.50(14) . . ? O1 C2 C18 106.90(16) . . ? O1 C2 C17 108.07(16) . . ? C18 C2 C17 110.66(16) . . ? O1 C2 C3 107.15(15) . . ? C18 C2 C3 108.79(16) . . ? C17 C2 C3 114.91(16) . . ? N4 C3 C8 109.21(16) . . ? N4 C3 C2 100.77(15) . . ? C8 C3 C2 115.08(16) . . ? C7 N4 C3 126.72(16) . . ? C7 N4 C5 92.20(15) . . ? C3 N4 C5 111.29(15) . . ? O1 C5 N4 104.62(15) . . ? O1 C5 C6 113.90(17) . . ? N4 C5 C6 89.97(15) . . ? C7 C6 C5 85.00(15) . . ? O7 C7 N4 130.45(19) . . ? O7 C7 C6 138.00(19) . . ? N4 C7 C6 91.55(16) . . ? O8 C8 O9 125.17(18) . . ? O8 C8 C3 123.56(18) . . ? O9 C8 C3 111.26(16) . . ? C8 O9 C10 114.53(14) . . ? O9 C10 C11 108.65(15) . . ? C16 C11 C12 119.58(19) . . ? C16 C11 C10 118.67(17) . . ? C12 C11 C10 121.71(18) . . ? C13 C12 C11 120.38(19) . . ? C14 C13 C12 118.13(18) . . ? C15 C14 C13 123.06(18) . . ? C15 C14 N14 118.91(17) . . ? C13 C14 N14 118.01(17) . . ? O14A N14 O14B 123.13(17) . . ? O14A N14 C14 118.45(16) . . ? O14B N14 C14 118.41(16) . . ? C14 C15 C16 117.87(18) . . ? C15 C16 C11 120.96(18) . . ? F17A C17 F17B 106.97(17) . . ? F17A C17 F17C 107.67(18) . . ? F17B C17 F17C 107.15(17) . . ? F17A C17 C2 111.10(17) . . ? F17B C17 C2 112.32(17) . . ? F17C C17 C2 111.37(17) . . ? F18A C18 F18C 108.15(17) . . ? F18A C18 F18B 106.73(17) . . ? F18C C18 F18B 107.47(17) . . ? F18A C18 C2 112.89(17) . . ? F18C C18 C2 111.63(17) . . ? F18B C18 C2 109.72(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.205 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.038