#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003717.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_2003717 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_volume 51 _journal_year 1995 _chemical_compound_source ; from chemical synthesis ; _chemical_formula_moiety 'C27 H39 N O8 S' _chemical_formula_sum 'C27 H39 N O8 S' _chemical_formula_weight 537.67 _chemical_name_systematic ; 4-benzyl-6-methoxy-3-propylsulfonyl-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 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _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 7.244(5) _cell_length_b 14.863(8) _cell_length_c 27.308(12) _cell_measurement_reflns_used 16 _cell_measurement_temperature 293 _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 4.0 _cell_volume 2940(3) _computing_data_collection 'Philips PW1100/20 software 1974' _computing_data_reduction 'PHIL (Riche, 1981)' _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 'Philips PW100 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 0.000 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2979 _diffrn_reflns_theta_max 68.01 _diffrn_reflns_theta_min 2.97 _diffrn_standards_decay_% 5 _diffrn_standards_interval_time 180 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.32 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.21 _exptl_crystal_description prism _exptl_crystal_F_000 1152.00 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.21 _refine_diff_density_min -0.35 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.10 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 319 _refine_ls_number_reflns 1656 _refine_ls_R_factor_obs 0.068 _refine_ls_shift/esd_max 0.06 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'calc w=1/[\s^2^(F) + 0.005220 F^2^]' _refine_ls_wR_factor_obs 0.093 _reflns_number_observed 1661 _reflns_number_total 2979 _reflns_observed_criterion refl_observed_if_I_>_2.5_sigma(I) _[local]_cod_data_source_file pa1154.cif _[local]_cod_data_source_block katia _cod_original_cell_volume 2940.(3) _cod_database_code 2003717 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z 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 0.6121(11) 0.9957(5) 0.2506(3) 0.051(7) Uani ? ? C2 0.6899(11) 1.0242(4) 0.2005(3) 0.051(7) Uani ? ? C3 0.5897(10) 0.9683(5) 0.1600(3) 0.050(7) Uani ? ? N4 0.4465(8) 0.9206(4) 0.1882(2) 0.050(6) Uani ? ? C5 0.4919(11) 0.9122(5) 0.2396(3) 0.048(7) Uani ? ? C6 0.2807(10) 0.9203(5) 0.2499(3) 0.052(7) Uani ? ? C7 0.2685(11) 0.9512(6) 0.1981(3) 0.058(8) Uani ? ? O8 0.1573(8) 0.9879(5) 0.1718(2) 0.080(7) Uani ? ? O9 0.2165(8) 0.9802(4) 0.2841(2) 0.059(6) Uani ? ? C10 0.2040(13) 0.9422(6) 0.3319(4) 0.079(11) Uani ? ? C11 0.7690(11) 0.9779(8) 0.2867(3) 0.073(10) Uani ? ? C12 0.7030(11) 0.9614(8) 0.3383(3) 0.069(10) Uani ? ? C13 0.6976(16) 0.8752(8) 0.3581(4) 0.090(13) Uani ? ? C14 0.6379(20) 0.8595(12) 0.4053(7) 0.126(21) Uani ? ? C15 0.5926(27) 0.9333(19) 0.4341(6) 0.155(29) Uani ? ? C16 0.5917(21) 1.0177(13) 0.4160(5) 0.123(20) Uani ? ? C17 0.6520(16) 1.0325(9) 0.3677(4) 0.092(13) Uani ? ? S18 0.6647(5) 1.1421(2) 0.1927(1) 0.094(4) Uani ? ? O19 0.7432(15) 1.1860(4) 0.2331(3) 0.126(12) Uani ? ? O20 0.4768(17) 1.1617(5) 0.1810(4) 0.136(14) Uani ? ? C21 0.8381(17) 1.1684(15) 0.1519(4) 0.095(7) Uiso ? ? C22 0.7708(31) 1.1500(15) 0.1010(3) 0.116(8) Uiso ? ? C23 0.8618(54) 1.2131(21) 0.0655(6) 0.177(14) Uiso ? ? C21' 0.7209(19) 1.1738(17) 0.1340(4) 0.115(9) Uiso ? ? C22' 0.9252(21) 1.1647(18) 0.1274(6) 0.118(9) Uiso ? ? C23' 0.9795(36) 1.2023(24) 0.0783(8) 0.186(15) Uiso ? ? C24 0.7194(12) 0.9034(4) 0.1354(3) 0.052(8) Uani ? ? C25 0.6326(13) 0.8369(5) 0.0996(3) 0.066(9) Uani ? ? C26 0.6407(15) 0.8617(8) 0.0478(4) 0.086(12) Uani ? ? C27 0.5249(25) 0.8047(10) 0.0137(5) 0.125(20) Uani ? ? O28 0.7996(8) 0.8476(3) 0.1713(2) 0.060(5) Uani ? ? O29 0.7362(11) 0.7580(4) 0.1063(3) 0.104(9) Uani ? ? O30 0.5631(11) 0.9482(5) 0.0414(2) 0.093(9) Uani ? ? O31 0.3557(15) 0.8483(10) 0.0132(4) 0.150(17) Uani ? ? C32 0.8276(17) 0.7600(6) 0.1518(4) 0.081(11) Uani ? ? C33 0.7459(33) 0.6972(8) 0.1890(6) 0.173(30) Uani ? ? C34 1.0288(21) 0.7428(11) 0.1435(5) 0.153(22) Uani ? ? C35 0.3947(20) 0.9427(11) 0.0150(4) 0.106(17) Uani ? ? C36 0.2369(23) 0.9833(14) 0.0422(5) 0.150(23) Uani ? ? C37 0.4153(22) 0.9782(15) -0.0350(5) 0.166(26) Uani ? ? H1 0.53590 1.04319 0.26683 0.056 Uiso calc C1 H2 0.82520 1.01152 0.19807 0.056 Uiso calc C2 H3 0.53923 1.00603 0.13285 0.055 Uiso calc C3 H5 0.55998 0.86241 0.25628 0.052 Uiso calc C5 H6 0.21064 0.86863 0.26420 0.057 Uiso calc C6 H10a 0.15666 0.98857 0.35530 0.086 Uiso calc C10 H10b 0.11752 0.88974 0.33135 0.086 Uiso calc C10 H10c 0.32891 0.92158 0.34274 0.086 Uiso calc C10 H11a 0.85295 1.03133 0.28681 0.080 Uiso calc C11 H11b 0.83926 0.92389 0.27536 0.080 Uiso calc C11 H13 0.73814 0.82312 0.33759 0.099 Uiso calc C13 H14 0.62738 0.79691 0.41836 0.138 Uiso calc C14 H15 0.55988 0.92356 0.46927 0.170 Uiso calc C15 H16 0.54869 1.06911 0.43669 0.135 Uiso calc C16 H17 0.65774 1.09523 0.35449 0.101 Uiso calc C17 H21a 0.94948 1.13083 0.15886 0.105 Uiso calc C21 H21b 0.87128 1.23345 0.15510 0.105 Uiso calc C21 H22a 0.63400 1.15855 0.09972 0.127 Uiso calc C22 H22b 0.80112 1.08650 0.09192 0.127 Uiso calc C22 H23a 0.81614 1.20031 0.03168 0.195 Uiso calc C23 H23b 0.83120 1.27655 0.07454 0.195 Uiso calc C23 H23c 0.99858 1.20439 0.06672 0.195 Uiso calc C23 H21'a 0.68320 1.23771 0.12847 0.127 Uiso calc C21' H21'b 0.65526 1.13428 0.11002 0.127 Uiso calc C22 H22'a 0.96058 1.09972 0.12912 0.130 Uiso calc C22' H22'b 0.99056 1.19845 0.15388 0.130 Uiso calc C21 H23'a 1.11594 1.19624 0.07386 0.204 Uiso calc C23' H23'b 0.91433 1.16841 0.05184 0.204 Uiso calc C23 H23'c 0.94435 1.26728 0.07665 0.204 Uiso calc C23 H24 0.80575 0.94345 0.11691 0.057 Uiso calc C24 H25 0.49744 0.83249 0.10668 0.073 Uiso calc C25 H26 0.77455 0.85529 0.03959 0.094 Uiso calc C26 H27a 0.51210 0.74201 0.02656 0.137 Uiso calc C27 H27b 0.58021 0.80266 -0.01979 0.137 Uiso calc C27 H33a 0.76077 0.63368 0.17757 0.190 Uiso calc C33 H33b 0.81071 0.70509 0.22102 0.190 Uiso calc C33 H33c 0.61167 0.71092 0.19316 0.190 Uiso calc C33 H34a 1.04591 0.68096 0.12984 0.168 Uiso calc C34 H34b 1.07874 0.78811 0.11994 0.168 Uiso calc C34 H34c 1.09650 0.74778 0.17535 0.168 Uiso calc C34 H36a 0.12185 0.97788 0.02212 0.164 Uiso calc C36 H36b 0.21970 0.95100 0.07396 0.164 Uiso calc C36 H36c 0.26302 1.04827 0.04867 0.164 Uiso calc C36 H37a 0.29470 0.97351 -0.05267 0.182 Uiso calc C37 H37b 0.45405 1.04274 -0.03348 0.182 Uiso calc C37 H37c 0.51100 0.94262 -0.05291 0.182 Uiso calc C37 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 0.0470(42) 0.0012(39) 0.0051(41) 0.0529(39) -0.0039(36) 0.0540(47) C2 0.0511(45) 0.0001(36) 0.0019(40) 0.0410(33) -0.0071(35) 0.0606(49) C3 0.0485(46) 0.0061(37) -0.0020(37) 0.0483(38) -0.0009(37) 0.0521(44) N4 0.0416(35) 0.0049(32) -0.0011(31) 0.0526(31) -0.0044(33) 0.0572(40) C5 0.0383(37) 0.0110(40) -0.0040(36) 0.0478(37) 0.0049(38) 0.0570(50) C6 0.0412(37) -0.0007(39) 0.0153(41) 0.0495(35) -0.0005(41) 0.0646(49) C7 0.0423(47) -0.0042(43) -0.0080(43) 0.0663(45) -0.0048(43) 0.0647(52) O8 0.0411(30) 0.0132(37) -0.0067(34) 0.1208(53) 0.0073(38) 0.0773(40) O9 0.0491(31) -0.0019(29) 0.0137(28) 0.0609(30) 0.0026(28) 0.0668(37) C10 0.0549(50) -0.0054(52) 0.0070(57) 0.0862(65) 0.0052(56) 0.0947(70) C11 0.0360(43) -0.0113(53) -0.0102(41) 0.1177(76) 0.0047(55) 0.0656(56) C12 0.0372(41) -0.0034(53) -0.0104(41) 0.1094(70) -0.0075(57) 0.0591(57) C13 0.0656(64) 0.0137(68) -0.0038(64) 0.1034(78) 0.0180(68) 0.1017(84) C14 0.0853(88) -0.0149(106) -0.0050(96) 0.1581(137) 0.0731(110) .1334(131) C15 0.1318(134) -0.0093(166) -0.0052(91) 0.2571(244) 0.0599(132) .0760(96) C16 0.1028(98) -0.0180(109) 0.0048(74) .1884(146) -0.0248(98) 0.0763(89) C17 0.0710(63) -0.0205(75) 0.0039(59) 0.1282(89) -0.0047(66) 0.0766(69) S18 0.1461(30) -0.0056(16) 0.0272(20) 0.0408(9) -0.0076(13) 0.0939(18) O19 0.1745(93) -0.0233(50) -0.0083(69) 0.0615(36) -0.0506(43) 0.1434(64) O20 0.1860(97) 0.0488(56) -0.0253(80) 0.0669(45) 0.0065(47) 0.1560(82) C24 0.0643(52) 0.0001(40) -0.0051(41) 0.0410(33) -0.0036(33) 0.0508(45) C25 0.0663(54) 0.0046(46) -0.0121(53) 0.0554(45) -0.0099(40) 0.0778(62) C26 0.0729(63) 0.0132(74) -0.0073(57) 0.1042(74) -0.0315(64) 0.0800(71) C27 0.1414(138) -0.0155(110) -0.0526(91) .1477(119) -0.0252(79) 0.0854(85) O28 0.0671(34) 0.0139(28) -0.0083(32) 0.0502(27) -0.0097(25) 0.0631(32) O29 0.1253(65) 0.0285(46) -0.0489(52) 0.0687(38) -0.0396(39) 0.1176(53) O30 0.0984(53) 0.0074(48) -0.0255(41) 0.1108(57) -0.0016(40) 0.0697(43) O31 0.1079(75) 0.0014(91) -0.0566(65) .2078(126) -0.0453(79) 0.1352(82) C32 0.0996(77) 0.0143(56) 0.0033(67) 0.0495(42) -0.0142(48) 0.0936(71) C33 0.2746(265) -0.0361(106) 0.0230(176) 0.0688(66) 0.0132(82) .1761(127) C34 0.1146(107) 0.0773(117) -0.0362(98) .1851(142) -0.1106(118) .1584(129) C35 0.0984(94) 0.0196(95) -0.0189(64) .1568(130) -0.0061(76) 0.0616(69) C36 0.1270(122) 0.0571(127) 0.0155(90) .2217(175) 0.0252(108) 0.0999(94) C37 0.1124(102) 0.0160(143) -0.0003(77) .3046(224) 0.0547(118) 0.0798(80) loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 0 0 4 0 0 0 6 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 104.7(6) yes C2 C1 C11 110.4(6) yes C5 C1 C11 114.0(6) yes C1 C2 C3 108.2(6) yes C1 C2 S18 109.9(5) yes C3 C2 S18 113.2(5) yes C2 C3 N4 102.4(6) yes C2 C3 C24 111.5(6) yes N4 C3 C24 111.4(6) yes C3 N4 C5 112.8(6) yes C3 N4 C7 126.7(6) yes C5 N4 C7 92.8(6) yes C1 C5 N4 104.3(6) yes C1 C5 C6 117.1(6) yes N4 C5 C6 86.9(5) yes C5 C6 C7 84.9(6) yes C5 C6 O9 120.3(6) yes C7 C6 O9 115.2(6) yes N4 C7 C6 91.7(6) yes N4 C7 O8 130.3(8) yes C6 C7 O8 138.0(8) yes C6 O9 C10 112.9(6) yes C1 C11 C12 113.3(7) yes C11 C12 C13 121.5(9) yes C11 C12 C17 120.2(9) yes C13 C12 C17 118.3(10) yes C12 C13 C14 121.8(12) yes C13 C14 C15 118.0(16) yes C14 C15 C16 121.9(19) yes C15 C16 C17 119.2(15) yes C12 C17 C16 120.5(11) yes C2 S18 O19 108.9(5) yes C2 S18 O20 109.1(5) yes C2 S18 C21 103.1(6) yes C2 S18 C21' 111.0(7) yes O19 S18 O20 117.9(6) yes O19 S18 C21 96.1(7) yes O19 S18 C21' 120.6(7) yes O20 S18 C21 120.2(7) yes O20 S18 C21' 87.8(7) yes S18 C21 C22 108.7(12) yes C21 C22 C23 110.0(18) yes S18 C21' C22' 108.8(13) yes C21' C22' C23' 109.4(18) yes C3 C24 C25 116.4(7) yes C3 C24 O28 108.8(6) yes C25 C24 O28 103.6(6) yes C24 C25 C26 116.1(8) yes C24 C25 O29 103.7(7) yes C26 C25 O29 108.4(8) yes C25 C26 C27 115.6(10) yes C25 C26 O30 109.4(8) yes C27 C26 O30 102.3(9) yes C26 C27 O31 103.6(11) yes C24 O28 C32 109.6(6) yes C25 O29 C32 110.5(7) yes C26 O30 C35 110.6(9) yes C27 O31 C35 106.5(12) yes O28 C32 O29 106.5(8) yes O28 C32 C33 105.1(10) yes O28 C32 C34 110.6(9) yes O29 C32 C33 113.4(10) yes O29 C32 C34 108.8(9) yes C33 C32 C34 112.3(11) yes O30 C35 O31 104.0(11) yes O30 C35 C36 112.5(12) yes O30 C35 C37 111.4(12) yes O31 C35 C36 105.2(12) yes O31 C35 C37 109.8(12) yes C36 C35 C37 113.3(13) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.541(11) yes C1 C5 1.545(10) yes C1 C11 1.527(11) yes C2 C3 1.560(10) yes C2 S18 1.774(7) yes C3 N4 1.472(10) yes C3 C24 1.506(11) yes N4 C5 1.448(10) yes N4 C7 1.394(10) yes C5 C6 1.560(11) yes C6 C7 1.488(12) yes C6 O9 1.371(9) yes C7 O8 1.210(10) yes O9 C10 1.427(12) yes C11 C12 1.510(12) yes C12 C13 1.391(16) yes C12 C17 1.377(16) yes C13 C14 1.38(2) yes C14 C15 1.39(3) yes C15 C16 1.35(3) yes C16 C17 1.409(18) yes S18 O19 1.402(9) yes S18 O20 1.428(12) yes S18 C21 1.725(13) yes S18 C21' 1.719(12) yes C21 C22 1.496(16) yes C22 C23 1.50(3) yes C21' C22' 1.50(2) yes C22' C23' 1.50(3) yes C24 C25 1.526(11) yes C24 O28 1.410(9) yes C25 C26 1.463(14) yes C25 O29 1.404(11) yes C26 C27 1.511(19) yes C26 O30 1.413(14) yes C27 O31 1.39(2) yes O28 C32 1.422(10) yes O29 C32 1.407(13) yes O30 C35 1.421(15) yes O31 C35 1.43(2) yes C32 C33 1.501(19) yes C32 C34 1.497(19) yes C35 C36 1.49(2) yes C35 C37 1.471(18) 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 9.4(6) yes C1 C2 C3 N4 7.0(6) yes C2 C3 N4 C5 -22.9(6) yes C3 N4 C5 C1 29.4(6) yes N4 C5 C1 C2 -22.4(6) yes C7 N4 C5 C6 14.7(8) yes N4 C5 C6 C7 -13.8(7) yes C5 C6 C7 N4 14.3(8) yes C6 C7 N4 C5 -15.4(8) yes O8 C7 C6 O9 -44.7(8) yes C1 C5 C6 O9 -25.6(6) yes C5 C6 O9 C10 -90.1(8) yes C6 C5 C1 C11 122.9(8) yes C5 C1 C11 C12 -69.9(8) yes C2 C1 C11 C12 172.6(10) yes C1 C11 C12 C13 103.4(11) yes C1 C11 C12 C17 -78.7(10) yes C11 C1 C2 C3 132.5(8) yes C11 C1 C2 S18 -103.5(7) yes C1 C2 C3 C24 -112.3(8) yes C1 C2 S18 O19 53.2(6) yes C1 C2 S18 O20 -76.7(6) yes C1 C2 S18 C21 154.5(8) yes C1 C2 S18 C21' -171.7(9) yes S18 C2 C3 C24 125.7(7) yes C2 C3 C24 C25 172.7(9) yes C2 C3 C24 O28 56.2(7) yes C3 C24 C25 C26 97.2(9) yes C3 C24 C25 O29 -144.0(9) yes C24 C25 C26 C27 -169.2(13) yes C24 C25 C26 O30 -54.4(9) yes C24 C25 O29 C32 20.0(8) yes C25 O29 C32 O28 -7.5(8) yes O29 C32 O28 C24 -9.6(7) yes C32 O28 C24 C25 21.2(7) yes O28 C24 C25 O29 -24.7(7) yes O29 C25 C26 C27 74.6(11) yes O29 C25 C26 O30 -170.6(11) yes O30 C26 C27 O31 -29.3(12) yes C26 C27 O31 C35 36.8(12) yes C27 O31 C35 O30 -29.8(12) yes O31 C35 O30 C26 10.1(10) yes C35 O30 C26 C27 11.3(10) yes C3 C2 S18 C21 -84.5(7) yes C3 C2 S18 C21' -50.7(7) yes C2 S18 C21 C22 83.2(10) yes S18 C21 C22 C23 149.8(19) yes C2 S18 C21' C22' -70.7(11) yes S18 C21' C22' C23' -173.(2) yes