#------------------------------------------------------------------------------ #$Date: 2014-09-06 05:12:35 +0300 (Sat, 06 Sep 2014) $ #$Revision: 123116 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/72/1517236.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1517236 loop_ _publ_author_name 'Logan, Angus W. J.' 'Sprague, Simon J.' 'Foster, Robert W.' 'Marx, L\'eo B' 'Garzya, Vincenzo' 'Hallside, Michal S.' 'Thompson, Amber L.' 'Burton, Jonathan W.' _publ_section_title ; Diastereoselective synthesis of fused lactone-pyrrolidinones; application to a formal synthesis of (-)-salinosporamide a. ; _journal_issue 16 _journal_name_full 'Organic letters' _journal_page_first 4078 _journal_page_last 4081 _journal_paper_doi 10.1021/ol501662t _journal_volume 16 _journal_year 2014 _chemical_formula_moiety 'C14 H13 N1 O5' _chemical_formula_sum 'C14 H13 N O5' _chemical_formula_weight 275.26 _chemical_melting_point ? _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary other _audit_creation_date 2013-09-04 _audit_creation_method CRYSTALS_ver_14.52 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 6.93860(10) _cell_length_b 15.1121(2) _cell_length_c 23.6998(3) _cell_measurement_reflns_used 3232 _cell_measurement_temperature 150 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 2485.09(6) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 36776 _diffrn_reflns_theta_full 27.486 _diffrn_reflns_theta_max 27.486 _diffrn_reflns_theta_min 5.162 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour clear_pale_colourless _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1152 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.37 _refine_diff_density_min -0.25 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9815 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2825 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0358 _refine_ls_shift/su_max 0.0002946 _refine_ls_shift/su_mean 0.0000348 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 9.97 13.0 3.91 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0788 _refine_ls_wR_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.0788 _reflns_limit_h_max 8 _reflns_limit_h_min 0 _reflns_limit_k_max 19 _reflns_limit_k_min 0 _reflns_limit_l_max 30 _reflns_limit_l_min 0 _reflns_number_gt 2263 _reflns_number_total 2825 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.12 _oxford_diffrn_Wilson_scale 4.48 _oxford_refine_ls_r_factor_ref 0.0482 _oxford_refine_ls_scale 0.4658(5) _oxford_reflns_number_all 2825 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_structure_analysis_title 007msh09 _[local]_cod_data_source_file ol501662t_si_002.cif _[local]_cod_data_source_block 10a _[local]_cod_cif_authors_sg_H-M 'P b c a ' _[local]_cod_chemical_formula_sum_orig 'C14 H13 N1 O5' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value 'not measured' was changed to '?' - the value is undefined or not given. '_atom_sites_solution_primary' value 'Other' changed to 'other' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius Adding full bibliography for 1517236--1517237.cif. ; _cod_database_code 1517236 _iucr_refine_instructions_details_constraints ; BLOCK SCALE X'S, U'S RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE N ( 13,X'S) H ( 131,X'S) RIDE C ( 15,X'S) H ( 152,X'S) H ( 151,X'S) RIDE C ( 19,X'S) H ( 193,X'S) H ( 192,X'S) H ( 191,X'S) END ; _iucr_refine_instructions_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn O1 O -0.01007(17) 0.59051(7) 0.44766(5) 0.0267 1.0000 Uani . C2 C -0.0034(2) 0.51447(10) 0.43306(6) 0.0208 1.0000 Uani . O3 O -0.15442(15) 0.45999(7) 0.43574(4) 0.0241 1.0000 Uani . C4 C -0.1056(2) 0.36874(9) 0.42146(6) 0.0208 1.0000 Uani . C5 C -0.2411(2) 0.33709(9) 0.37612(6) 0.0209 1.0000 Uani . C6 C -0.2946(2) 0.24870(11) 0.37540(7) 0.0286 1.0000 Uani . C7 C -0.4186(3) 0.21743(11) 0.33350(7) 0.0335 1.0000 Uani . C8 C -0.4902(2) 0.27434(11) 0.29301(7) 0.0295 1.0000 Uani . C9 C -0.4361(2) 0.36244(11) 0.29338(7) 0.0310 1.0000 Uani . C10 C -0.3118(2) 0.39350(10) 0.33464(7) 0.0283 1.0000 Uani . C11 C 0.1114(2) 0.36839(9) 0.40447(6) 0.0202 1.0000 Uani . C12 C 0.1755(2) 0.46592(9) 0.41004(6) 0.0185 1.0000 Uani . N13 N 0.32953(17) 0.46641(8) 0.45043(5) 0.0191 1.0000 Uani . C14 C 0.3701(2) 0.38638(10) 0.47261(6) 0.0208 1.0000 Uani . C15 C 0.2450(2) 0.31724(10) 0.44445(7) 0.0250 1.0000 Uani . O16 O 0.49179(16) 0.37209(7) 0.50931(5) 0.0271 1.0000 Uani . C17 C 0.2229(2) 0.51083(9) 0.35395(6) 0.0212 1.0000 Uani . O18 O 0.38317(16) 0.55775(8) 0.35645(5) 0.0296 1.0000 Uani . C19 C 0.4308(3) 0.60699(13) 0.30567(7) 0.0383 1.0000 Uani . O20 O 0.11702(17) 0.50598(8) 0.31376(4) 0.0314 1.0000 Uani . H41 H -0.1241 0.3356 0.4571 0.0271 1.0000 Uiso R H61 H -0.2472 0.2083 0.4032 0.0357 1.0000 Uiso R H71 H -0.4535 0.1595 0.3331 0.0383 1.0000 Uiso R H81 H -0.5784 0.2507 0.2656 0.0363 1.0000 Uiso R H91 H -0.4834 0.3994 0.2651 0.0399 1.0000 Uiso R H101 H -0.2730 0.4548 0.3351 0.0346 1.0000 Uiso R H111 H 0.1223 0.3510 0.3634 0.0229 1.0000 Uiso R H152 H 0.3300 0.2732 0.4234 0.0332 1.0000 Uiso R H151 H 0.1734 0.2850 0.4726 0.0329 1.0000 Uiso R H193 H 0.5580 0.6313 0.3124 0.0604 1.0000 Uiso R H192 H 0.4441 0.5654 0.2743 0.0597 1.0000 Uiso R H191 H 0.3351 0.6499 0.2965 0.0600 1.0000 Uiso R H131 H 0.3857 0.5167 0.4640 0.0327 1.0000 Uiso 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 0.0296(6) 0.0230(5) 0.0274(5) -0.0045(4) -0.0004(4) 0.0040(5) C2 0.0207(7) 0.0251(7) 0.0166(6) -0.0016(5) -0.0012(5) 0.0020(6) O3 0.0187(5) 0.0263(5) 0.0274(5) -0.0073(4) 0.0029(4) 0.0010(4) C4 0.0192(7) 0.0221(7) 0.0210(7) -0.0020(5) 0.0012(5) 0.0006(6) C5 0.0156(6) 0.0254(7) 0.0216(6) -0.0025(5) 0.0020(5) -0.0014(5) C6 0.0296(8) 0.0258(7) 0.0305(8) 0.0033(6) -0.0034(6) -0.0045(7) C7 0.0361(9) 0.0274(8) 0.0370(9) -0.0041(7) -0.0035(7) -0.0092(7) C8 0.0234(7) 0.0380(9) 0.0271(7) -0.0092(7) -0.0020(6) -0.0028(7) C9 0.0298(8) 0.0354(9) 0.0280(8) 0.0007(6) -0.0069(7) 0.0008(7) C10 0.0287(8) 0.0247(7) 0.0316(8) 0.0018(6) -0.0057(6) -0.0031(6) C11 0.0166(6) 0.0215(7) 0.0224(6) -0.0033(5) -0.0003(5) -0.0001(5) C12 0.0173(6) 0.0199(6) 0.0181(6) -0.0019(5) 0.0001(5) 0.0000(5) N13 0.0184(6) 0.0198(6) 0.0192(5) -0.0008(4) -0.0036(5) -0.0011(5) C14 0.0166(6) 0.0239(7) 0.0218(7) -0.0008(5) 0.0005(5) 0.0010(5) C15 0.0207(7) 0.0193(7) 0.0349(8) -0.0020(6) -0.0046(6) 0.0016(6) O16 0.0252(5) 0.0257(5) 0.0305(6) 0.0029(4) -0.0077(5) 0.0008(4) C17 0.0219(7) 0.0224(7) 0.0192(6) -0.0014(5) 0.0021(5) 0.0032(6) O18 0.0264(5) 0.0374(6) 0.0251(5) 0.0081(5) 0.0014(4) -0.0063(5) C19 0.0355(9) 0.0480(10) 0.0315(9) 0.0143(8) 0.0083(7) -0.0057(8) O20 0.0348(6) 0.0389(6) 0.0205(5) 0.0020(5) -0.0060(5) -0.0029(5) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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 O1 C2 O3 123.11(14) yes O1 C2 C12 126.06(14) yes O3 C2 C12 110.82(11) yes C2 O3 C4 112.93(11) yes O3 C4 C5 108.71(11) yes O3 C4 C11 106.69(11) yes C5 C4 C11 114.69(11) yes O3 C4 H41 104.5 no C5 C4 H41 111.5 no C11 C4 H41 110.1 no C4 C5 C6 118.81(13) yes C4 C5 C10 122.00(13) yes C6 C5 C10 119.19(14) yes C5 C6 C7 119.98(15) yes C5 C6 H61 120.9 no C7 C6 H61 119.1 no C6 C7 C8 120.34(15) yes C6 C7 H71 119.9 no C8 C7 H71 119.8 no C7 C8 C9 119.81(15) yes C7 C8 H81 117.9 no C9 C8 H81 122.3 no C8 C9 C10 119.97(15) yes C8 C9 H91 118.5 no C10 C9 H91 121.6 no C5 C10 C9 120.70(15) yes C5 C10 H101 118.9 no C9 C10 H101 120.4 no C4 C11 C12 104.63(11) yes C4 C11 C15 115.19(12) yes C12 C11 C15 104.72(11) yes C4 C11 H111 108.7 no C12 C11 H111 108.0 no C15 C11 H111 114.8 no C2 C12 C11 104.65(11) yes C2 C12 N13 111.17(11) yes C11 C12 N13 106.03(11) yes C2 C12 C17 105.65(11) yes C11 C12 C17 114.28(11) yes N13 C12 C17 114.68(12) yes C12 N13 C14 114.26(12) yes C12 N13 H131 123.9 no C14 N13 H131 121.3 no N13 C14 C15 109.12(12) yes N13 C14 O16 125.16(13) yes C15 C14 O16 125.71(13) yes C11 C15 C14 105.72(11) yes C11 C15 H152 112.1 no C14 C15 H152 109.5 no C11 C15 H151 111.8 no C14 C15 H151 109.9 no H152 C15 H151 107.8 no C12 C17 O18 112.39(12) yes C12 C17 O20 121.95(14) yes O18 C17 O20 125.57(14) yes C17 O18 C19 115.44(12) yes O18 C19 H193 105.4 no O18 C19 H192 108.7 no H193 C19 H192 106.4 no O18 C19 H191 112.3 no H193 C19 H191 114.5 no H192 C19 H191 109.3 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.2009(17) yes C2 O3 1.3343(18) yes C2 C12 1.5413(19) yes O3 C4 1.4597(17) yes C4 C5 1.5058(19) yes C4 C11 1.5589(19) yes C4 H41 0.991 no C5 C6 1.386(2) yes C5 C10 1.391(2) yes C6 C7 1.396(2) yes C6 H61 0.957 no C7 C8 1.381(2) yes C7 H71 0.909 no C8 C9 1.383(2) yes C8 H81 0.961 no C9 C10 1.386(2) yes C9 H91 0.933 no C10 H101 0.965 no C11 C12 1.5451(19) yes C11 C15 1.534(2) yes C11 H111 1.011 no C12 N13 1.4350(17) yes C12 C17 1.5285(19) yes N13 C14 1.3484(18) yes N13 H131 0.912 no C14 C15 1.513(2) yes C14 O16 1.2313(17) yes C15 H152 1.019 no C15 H151 0.964 no C17 O18 1.3203(18) yes C17 O20 1.2050(18) yes O18 C19 1.4530(18) yes C19 H193 0.969 no C19 H192 0.978 no C19 H191 0.954 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C9 H91 O20 8_455 143.63 0.933 2.563 3.360(2) yes C19 H192 O20 8_555 152.35 0.978 2.570 3.466(2) yes N13 H131 O16 2_666 177.86 0.912 1.987 2.899(2) yes