#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003718.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2003718 loop_ _publ_author_name 'Chiaroni, A.' 'Riche, C.' 'Adonias, M.' 'Anaya, J.' 'G\'ero, S. D.' 'Tachdjian, C.' _publ_section_title ; Two Methyl-Substituted Carbapenem Antibiotic Precursors ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1306 _journal_page_last 1310 _journal_paper_doi 10.1107/S0108270194014423 _journal_volume 51 _journal_year 1995 _chemical_compound_source ' from chemical synthesis' _chemical_formula_moiety 'C24 H35 N O7 S' _chemical_formula_sum 'C24 H35 N O7 S' _chemical_formula_weight 481.61 _chemical_name_systematic ; 3-ethylsulfuryl-4-furan-2-yl-methyl-6-methoxy-2- (2,2,2',2'-tetramethyl-[4,4']bi[[1,3] dioxolanyl]-5-yl) -1-aza-bicyclo[3.2.0] heptane-7-one ; _space_group_IT_number 76 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall 'P 4w' _symmetry_space_group_name_H-M 'P 41' _atom_type_scat_source 'IntTabIV Table 2.2B' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.136(6) _cell_length_b 10.136(6) _cell_length_c 25.026(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 16.3 _cell_measurement_theta_min 8.1 _cell_volume 2571(2) _computing_data_collection 'Nonius CAD4 software 1987' _computing_data_reduction 'NONIUS (Riche, 1989) ' _computing_molecular_graphics 'R3M (Riche,1983) ORTEP (Johnson, 1963)' _computing_publication_material 'ACTACIF (Riche, 1992)' _computing_structure_refinement 'SHELX76 (Sheldrick, 1976)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Nonius CAD4 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4718 _diffrn_reflns_theta_max 64.74 _diffrn_reflns_theta_min 3.53 _diffrn_standards_decay_% 4 _diffrn_standards_interval_time 166 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.43 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.24 _exptl_crystal_description prism _exptl_crystal_F_000 1032.00 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.23 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 0.61 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 295 _refine_ls_number_reflns 1801 _refine_ls_R_factor_obs 0.048 _refine_ls_shift/esd_max 0.04 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.000124F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.052 _reflns_number_observed 1807 _reflns_number_total 2231 _reflns_observed_criterion refl_observed_if_I_>_3.0_sigma(I) _[local]_cod_data_source_file pa1154.cif _[local]_cod_data_source_block adonias _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(F) + 0.000124F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F) + 0.000124F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2571.(2) _cod_database_code 2003718 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,1/2+z -y,+x,1/4+z +y,-x,3/4+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 C1 0.0502(24) 0.0044(21) 0.0012(21) 0.0519(25) -0.0064(21) 0.0497(27) C2 0.0581(28) 0.0023(21) 0.0022(23) 0.0442(24) -0.0056(22) 0.0576(30) C3 0.0484(25) 0.0046(21) 0.0029(22) 0.0484(24) -0.0060(23) 0.0520(26) N4 0.0530(22) 0.0099(19) -0.0062(19) 0.0554(22) -0.0023(20) 0.0538(24) C5 0.0638(30) 0.0083(24) -0.0063(23) 0.0598(28) -0.0117(22) 0.0406(25) C6 0.0847(40) 0.0157(29) 0.0045(28) 0.0704(34) 0.0130(25) 0.0463(28) C7 0.0679(31) 0.0124(25) -0.0080(24) 0.0539(29) 0.0074(24) 0.0458(27) O8 0.1114(30) 0.0216(20) 0.0104(23) 0.0516(20) 0.0089(20) 0.0749(26) O9 0.0762(26) -0.0018(20) 0.0219(25) 0.0739(27) 0.0224(25) 0.1171(35) C10 0.1447(71) -0.0084(52) 0.0487(70) 0.0822(49) 0.0459(59) 0.2105(101) C11 0.0751(34) 0.0240(27) 0.0077(26) 0.0660(30) -0.0097(25) 0.0500(28) C12 0.0712(35) 0.0215(29) 0.0180(31) 0.0718(34) -0.0094(30) 0.0715(38) O13 0.1004(33) 0.0161(29) -0.0282(33) 0.1082(34) -0.0025(32) 0.1257(40) C14 0.1197(68) 0.0689(68) -0.0361(55) 0.1613(83) -0.0308(72) 0.1186(66) C15 0.1519(83) 0.0840(64) 0.0201(54) 0.1375(69) 0.0046(56) 0.0798(47) C16 0.1022(49) 0.0310(37) 0.0209(50) 0.0740(40) 0.0112(45) 0.1369(61) S17 0.0963(11) -0.0123(7) 0.0174(11) 0.0521(8) -0.0190(9) 0.1202(14) C20 0.0476(24) 0.0022(20) 0.0041(22) 0.0410(22) -0.0006(21) 0.0496(27) C21 0.0446(24) 0.0012(21) -0.0011(23) 0.0543(26) -0.0063(24) 0.0621(29) C22 0.0551(29) 0.0030(26) 0.0106(26) 0.0737(34) -0.0089(28) 0.0655(33) C23 0.0692(36) 0.0050(33) 0.0214(35) 0.0915(44) -0.0311(37) 0.0925(45) O24 0.0447(16) -0.0014(15) -0.0017(15) 0.0551(18) -0.0082(16) 0.0561(19) O25 0.0565(20) 0.0039(18) -0.0071(21) 0.0622(21) -0.0394(21) 0.1110(31) O26 0.0525(20) -0.0053(19) 0.0138(21) 0.0723(23) -0.0203(22) 0.1065(31) O27 0.0958(31) 0.0192(26) -0.0287(35) 0.0875(31) -0.0092(32) 0.1597(48) C28 0.0557(29) 0.0032(24) -0.0064(26) 0.0552(29) -0.0121(27) 0.0720(35) C29 0.0846(39) -0.0216(31) -0.0107(35) 0.0632(33) -0.0113(32) 0.0982(42) C30 0.1036(45) 0.0010(35) -0.0090(34) 0.0879(41) -0.0134(32) 0.0630(35) C31 0.0765(37) -0.0039(31) -0.0028(31) 0.0750(36) -0.0075(31) 0.0739(38) C32 0.1904(92) -0.0672(71) -0.0253(59) 0.1769(86) 0.0393(58) 0.0892(61) C33 0.0582(32) -0.0012(36) 0.0178(32) 0.1337(58) -0.0054(45) 0.0948(49) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom C1 1.1475(4) 0.4068(4) 0.2196(2) 0.051(4) Uani ? ? C2 1.0471(5) 0.3559(4) 0.2616(2) 0.053(5) Uani ? ? C3 0.9488(4) 0.4714(4) 0.2695(2) 0.050(4) Uani ? ? N4 0.9682(4) 0.5516(4) 0.2209(2) 0.054(4) Uani ? ? C5 1.0603(5) 0.4891(5) 0.1837(2) 0.055(5) Uani ? ? C6 1.1031(6) 0.6261(6) 0.1650(2) 0.067(6) Uani ? ? C7 1.0139(5) 0.6772(5) 0.2100(2) 0.056(5) Uani ? ? O8 0.9909(4) 0.7828(3) 0.2289(2) 0.079(4) Uani ? ? O9 1.2367(4) 0.6497(4) 0.1710(2) 0.089(5) Uani ? ? C10 1.2728(10) 0.7743(7) 0.1506(5) 0.146(13) Uani ? ? C11 1.2311(5) 0.3031(5) 0.1898(2) 0.064(5) Uani ? ? C12 1.3178(6) 0.2209(6) 0.2227(2) 0.072(6) Uani ? ? O13 1.4272(5) 0.2778(5) 0.2417(2) 0.111(6) Uani ? ? C14 1.4942(9) 0.1815(11) 0.2694(4) 0.133(13) Uani ? ? C15 1.4330(11) 0.0703(10) 0.2675(4) 0.123(12) Uani ? ? C16 1.3179(7) 0.0932(6) 0.2370(4) 0.104(9) Uani ? ? S17 0.9629(2) 0.2080(1) 0.2385 0.090(2) Uani ? ? C18 0.8906(11) 0.1616(10) 0.3007(3) 0.107(4) Uiso ? ? C19 0.8286(11) 0.0380(9) 0.3035(5) 0.104(3) Uiso ? ? C18' 0.9795(21) 0.0752(13) 0.2835(6) 0.101(6) Uiso ? ? C19' 0.9104(19) 0.1154(20) 0.3290(8) 0.090(6) Uiso ? ? C20 0.9674(4) 0.5450(4) 0.3219(2) 0.046(4) Uani ? ? C21 0.8722(4) 0.6597(4) 0.3331(2) 0.054(5) Uani ? ? C22 0.7533(5) 0.6193(5) 0.3665(2) 0.065(6) Uani ? ? C23 0.6607(6) 0.7300(6) 0.3782(3) 0.084(7) Uani ? ? O24 1.0942(3) 0.6044(3) 0.3246(2) 0.052(3) Uani ? ? O25 0.9505(3) 0.7484(3) 0.3635(2) 0.077(4) Uani ? ? O26 0.6768(3) 0.5283(4) 0.3365(2) 0.077(4) Uani ? ? O27 0.5712(5) 0.7244(5) 0.3355(3) 0.114(7) Uani ? ? C28 1.0853(5) 0.7102(5) 0.3625(2) 0.061(5) Uani ? ? C29 1.1684(6) 0.8226(5) 0.3427(3) 0.082(7) Uani ? ? C30 1.1250(7) 0.6641(6) 0.4173(3) 0.085(7) Uani ? ? C31 0.5580(6) 0.5931(6) 0.3197(3) 0.075(6) Uani ? ? C32 0.5471(12) 0.5884(10) 0.2599(4) 0.152(14) Uani ? ? C33 0.4448(6) 0.5200(8) 0.3456(3) 0.096(8) Uani ? ? H1 1.22141 0.45612 0.23701 0.056 Uiso calc C1 H2 1.09133 0.33016 0.29573 0.059 Uiso calc C2 H3 0.85514 0.44169 0.27323 0.055 Uiso calc C3 H5 1.04201 0.42614 0.15381 0.060 Uiso calc C5 H6 1.09454 0.65830 0.12738 0.074 Uiso calc C6 H10a 1.36978 0.78795 0.15562 0.160 Uiso calc C10 H10b 1.25102 0.77874 0.11170 0.160 Uiso calc C10 H10c 1.22340 0.84486 0.17013 0.160 Uiso calc C10 H11a 1.28743 0.35079 0.16326 0.070 Uiso calc C11 H11b 1.16917 0.24318 0.17029 0.070 Uiso calc C11 H14 1.57955 0.19615 0.28861 0.147 Uiso calc C14 H15 1.46118 -0.01483 0.28425 0.135 Uiso calc C15 H16 1.24898 0.02636 0.22773 0.115 Uiso calc C16 H18a 0.82325 0.22989 0.31000 0.118 Uiso calc C18 H18b 0.96222 0.16258 0.32823 0.118 Uiso calc C18 H19a 0.79248 0.02422 0.34028 0.115 Uiso calc C19 H19b 0.75485 0.03445 0.27698 0.115 Uiso calc C19 H19c 0.89402 -0.03297 0.29525 0.115 Uiso calc C19 H18'a 1.07450 0.05905 0.29207 0.111 Uiso calc C18' H18'b 0.94026 -0.00706 0.26819 0.111 Uiso calc C18' H19'a 0.91506 0.04468 0.35679 0.099 Uiso calc C19' H19'b 0.95046 0.19829 0.34337 0.099 Uiso calc C18 H19'c 0.81601 0.13208 0.31945 0.099 Uiso calc C18 H20 0.95149 0.47326 0.34850 0.051 Uiso calc C20 H21 0.83548 0.69614 0.29906 0.059 Uiso calc C21 H22 0.79007 0.58374 0.40072 0.071 Uiso calc C22 H23a 0.70817 0.81647 0.37893 0.093 Uiso calc C23 H23b 0.61480 0.71639 0.41315 0.093 Uiso calc C23 H29a 1.16351 0.89747 0.36862 0.090 Uiso calc C29 H29b 1.26206 0.79293 0.33912 0.090 Uiso calc C29 H29c 1.13499 0.85236 0.30707 0.090 Uiso calc C29 H30a 1.11819 0.73917 0.44313 0.093 Uiso calc C30 H30b 1.06526 0.59109 0.42900 0.093 Uiso calc C30 H30c 1.21809 0.63140 0.41641 0.093 Uiso calc C30 H32a 0.46409 0.63364 0.24842 0.167 Uiso calc C32 H32b 0.62472 0.63396 0.24358 0.167 Uiso calc C32 H32c 0.54502 0.49437 0.24778 0.167 Uiso calc C32 H33a 0.35949 0.56195 0.33488 0.105 Uiso calc C33 H33b 0.44561 0.42585 0.33366 0.105 Uiso calc C33 H33c 0.45436 0.52390 0.38530 0.105 Uiso calc C33 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -2 1 2 -3 1 -2 1 5 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 C5 101.7(4) yes C2 C1 C11 117.5(4) yes C5 C1 C11 114.1(4) yes C1 C2 C3 104.9(4) yes C1 C2 S17 111.6(3) yes C3 C2 S17 111.2(3) yes C2 C3 N4 103.0(4) yes C2 C3 C20 113.6(4) yes N4 C3 C20 115.1(4) yes C3 N4 C5 111.8(4) yes C3 N4 C7 135.6(4) yes C5 N4 C7 93.4(4) yes C1 C5 N4 103.5(4) yes C1 C5 C6 121.2(4) yes N4 C5 C6 89.0(4) yes C5 C6 C7 85.1(4) yes C5 C6 O9 113.7(5) yes C7 C6 O9 116.0(5) yes N4 C7 C6 91.8(4) yes N4 C7 O8 133.0(5) yes C6 C7 O8 135.2(5) yes C6 O9 C10 111.8(5) yes C1 C11 C12 116.3(4) yes C11 C12 O13 116.9(5) yes C11 C12 C16 134.3(6) yes O13 C12 C16 108.7(6) yes C12 O13 C14 106.4(6) yes O13 C14 C15 111.4(9) yes C14 C15 C16 105.9(9) yes C12 C16 C15 107.6(7) yes C2 S17 C18 97.6(3) yes C2 S17 C18' 112.4(6) yes S17 C18 C19 117.6(7) yes S17 C18' C19' 104.5(12) yes C3 C20 C21 116.8(4) yes C3 C20 O24 111.2(4) yes C21 C20 O24 103.8(3) yes C20 C21 C22 113.2(4) yes C20 C21 O25 103.1(4) yes C22 C21 O25 108.5(4) yes C21 C22 C23 113.8(5) yes C21 C22 O26 108.4(4) yes C23 C22 O26 104.4(4) yes C22 C23 O27 103.1(5) yes C20 O24 C28 106.9(3) yes C21 O25 C28 110.8(4) yes C22 O26 C31 108.5(4) yes C23 O27 C31 108.5(5) yes O24 C28 O25 106.0(4) yes O24 C28 C29 108.3(4) yes O24 C28 C30 110.8(4) yes O25 C28 C29 109.8(4) yes O25 C28 C30 109.0(4) yes C29 C28 C30 112.8(5) yes O26 C31 O27 105.8(5) yes O26 C31 C32 109.9(6) yes O26 C31 C33 106.7(5) yes O27 C31 C32 108.7(6) yes O27 C31 C33 114.7(5) yes C32 C31 C33 110.8(6) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.551(7) yes C1 C5 1.512(7) yes C1 C11 1.543(7) yes C2 C3 1.550(6) yes C2 S17 1.819(5) yes C3 N4 1.476(6) yes C3 C20 1.520(7) yes N4 C5 1.463(6) yes N4 C7 1.382(6) yes C5 C6 1.528(7) yes C6 C7 1.534(8) yes C6 O9 1.383(7) yes C7 O8 1.194(6) yes O9 C10 1.410(9) yes C11 C12 1.466(8) yes C12 O13 1.337(8) yes C12 C16 1.343(9) yes O13 C14 1.376(12) yes C14 C15 1.288(15) yes C15 C16 1.414(13) yes S17 C18 1.784(8) yes S17 C18' 1.762(13) yes C18 C19 1.404(14) yes C18' C19' 1.40(3) yes C20 C21 1.536(6) yes C20 O24 1.421(5) yes C21 C22 1.524(7) yes C21 O25 1.420(6) yes C22 C23 1.492(8) yes C22 O26 1.420(7) yes C23 O27 1.403(9) yes O24 C28 1.435(6) yes O25 C28 1.421(6) yes O26 C31 1.435(7) yes O27 C31 1.395(8) yes C28 C29 1.501(8) yes C28 C30 1.505(8) yes C31 C32 1.501(11) yes C31 C33 1.512(9) yes 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_publ_flag C5 C1 C2 C3 -35.7(4) yes C1 C2 C3 N4 19.7(4) yes C2 C3 N4 C5 4.4(4) yes C3 N4 C5 C1 -27.2(4) yes N4 C5 C1 C2 37.7(4) yes C7 N4 C5 C6 -6.5(5) yes N4 C5 C6 C7 5.9(5) yes C5 C6 C7 N4 -6.3(5) yes C6 C7 N4 C5 6.5(5) yes O8 C7 C6 O9 59.9(6) yes C7 C6 O9 C10 -86.8(6) yes C1 C5 C6 O9 17.0(4) yes C5 C6 O9 C10 176.8(7) yes C6 C5 C1 C11 -97.6(5) yes C5 C1 C11 C12 179.8(6) yes C2 C1 C11 C12 -61.4(5) yes C1 C11 C12 O13 -74.6(6) yes C1 C11 C12 C16 109.9(7) yes C11 C1 C2 S17 -40.5(4) yes C1 C2 S17 C18 167.3(5) yes C2 S17 C18 C19 -171.3(7) yes C1 C2 S17 C18' 124.2(7) yes C2 S17 C18' C19' 66.3(11) yes C11 C1 C2 C3 -161.0(5) yes C1 C2 C3 C20 -105.4(5) yes S17 C2 C3 C20 133.8(4) yes C2 C3 C20 C21 -179.1(5) yes C2 C3 C20 O24 62.1(4) yes C7 N4 C3 C20 8.6(4) yes N4 C3 C20 O24 -56.4(4) yes C3 C20 C21 C22 94.6(5) yes C20 C21 C22 C23 179.4(6) yes O25 C21 C22 C23 65.7(5) yes C20 C21 C22 O26 -65.0(5) yes O24 C20 C21 O25 -25.6(4) yes C20 C21 O25 C28 11.0(4) yes C21 O25 C28 O24 7.6(4) yes O25 C28 O24 C20 -24.9(4) yes C28 O24 C20 C21 31.1(4) yes C21 C22 C23 O27 90.7(6) yes O26 C22 C23 O27 -27.2(5) yes C22 C23 O27 C31 31.8(5) yes C23 O27 C31 O26 -23.9(5) yes O27 C31 O26 C22 5.4(5) yes C31 O26 C22 C23 13.5(5) yes