#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2010620.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_2010620 loop_ _publ_author_name 'Camus, Fabrice' 'Norberg, Bernadette' 'Legrand, Anne' 'Rigo, Benoit' 'Durant, Fran\,cois' 'Wouters, Johan' _publ_section_title ; Structural analysis of pyrrolidinones ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 193 _journal_page_last 196 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C23 H27 N O7' _chemical_formula_weight 429.46 _chemical_name_systematic ; 'methyl N-[4-methoxyphenyl-(3,4,5-trimethoxyphenyl)-methyl] pyroglutamate' ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.538(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.4810(10) _cell_length_b 14.2060(10) _cell_length_c 18.2730(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 42 _cell_measurement_theta_min 30 _cell_volume 2201.5(3) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1992)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .960 _diffrn_measured_fraction_theta_max .960 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .023 _diffrn_reflns_av_sigmaI/netI .0102 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 6885 _diffrn_reflns_theta_full 71.91 _diffrn_reflns_theta_max 71.91 _diffrn_reflns_theta_min 3.94 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time '60 min' _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .797 _exptl_absorpt_correction_T_max .8569 _exptl_absorpt_correction_T_min .7960 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 912 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .20 _refine_diff_density_max .304 _refine_diff_density_min -.239 _refine_ls_extinction_coef .0104(5) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 283 _refine_ls_number_reflns 4331 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all .0456 _refine_ls_R_factor_gt .0424 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.5599P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref .1221 _reflns_number_gt 3939 _reflns_number_total 4331 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gs1054.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2010620 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 .18619(14) 1.00402(9) .61066(7) .0361(3) Uani d . 1 C H1 .1554 .9556 .5751 .041(4) Uiso calc R 1 H C2 .09036(15) .98528(10) .67946(7) .0374(3) Uani d . 1 C C3 .07918(16) 1.05288(10) .73415(7) .0418(3) Uani d . 1 C H3 .1264 1.1114 .7281 .050 Uiso calc R 1 H C4 -.00259(16) 1.03301(10) .79801(7) .0429(3) Uani d . 1 C C5 -.08024(16) .94753(11) .80531(8) .0444(3) Uani d . 1 C C6 -.07112(17) .88028(10) .74967(8) .0457(3) Uani d . 1 C C7 .01611(16) .89900(10) .68711(8) .0426(3) Uani d . 1 C H7 .0245 .8537 .6506 .051 Uiso calc R 1 H C8 .14805(14) 1.09832(9) .57526(7) .0357(3) Uani d . 1 C C9 -.00909(15) 1.11973(10) .55837(8) .0430(3) Uani d . 1 C H9 -.0877 1.0772 .5709 .052 Uiso calc R 1 H C10 -.05032(16) 1.20224(11) .52363(8) .0474(3) Uani d . 1 C H10 -.1557 1.2146 .5128 .057 Uiso calc R 1 H C11 .06505(17) 1.26717(10) .50473(7) .0423(3) Uani d . 1 C C12 .22165(16) 1.24640(10) .51951(8) .0423(3) Uani d . 1 C H12 .3002 1.2886 .5063 .051 Uiso calc R 1 H C13 .26136(15) 1.16236(10) .55424(7) .0399(3) Uani d . 1 C H13 .3670 1.1490 .5635 .048 Uiso calc R 1 H N18 .35550(12) .99215(8) .62385(6) .0364(3) Uani d . 1 N C19 .44662(15) .93779(10) .58019(7) .0396(3) Uani d . 1 C C20 .61516(16) .94527(11) .60725(9) .0487(4) Uani d . 1 C H20A .6868 .9543 .5668 .058 Uiso calc R 1 H H20B .6460 .8891 .6340 .058 Uiso calc R 1 H C21 .61482(16) 1.03054(11) .65699(8) .0470(3) Uani d . 1 C H21A .6447 1.0868 .6305 .056 Uiso calc R 1 H H21B .6868 1.0219 .6980 .056 Uiso calc R 1 H C22 .44251(16) 1.03722(10) .68332(7) .0397(3) Uani d . 1 C H22 .4111 1.1034 .6872 .039(4) Uiso calc R 1 H O23 -.01575(15) 1.09367(8) .85571(6) .0587(3) Uani d . 1 O C24 .0839(3) 1.17375(14) .85756(11) .0748(6) Uani d . 1 C H24A .0562 1.2152 .8180 .112 Uiso calc R 1 H H24B .1916 1.1542 .8527 .112 Uiso calc R 1 H H24C .0712 1.2061 .9033 .112 Uiso calc R 1 H O25 -.17314(14) .93136(9) .86548(6) .0590(3) Uani d . 1 O C26 -.0987(3) .8828(2) .92358(12) .0932(8) Uani d . 1 C H26A -.0708 .8206 .9078 .140 Uiso calc R 1 H H26B -.1694 .8787 .9642 .140 Uiso calc R 1 H H26C -.0052 .9162 .9383 .140 Uiso calc R 1 H O27 -.15295(16) .79920(9) .76148(7) .0674(4) Uani d . 1 O C28 -.1511(3) .72962(12) .70627(12) .0687(5) Uani d . 1 C H28A -.1929 .7554 .6616 .103 Uiso calc R 1 H H28B -.2143 .6770 .7211 .103 Uiso calc R 1 H H28C -.0446 .7091 .6987 .103 Uiso calc R 1 H O29 .39798(12) .89150(8) .52828(6) .0542(3) Uani d . 1 O C30 .42565(18) .98921(11) .75696(8) .0471(3) Uani d . 1 C O31 .42619(18) .89685(9) .75173(6) .0674(4) Uani d . 1 O C32 .4234(4) .84702(18) .82092(11) .1054(10) Uani d . 1 C H32A .4593 .7836 .8139 .158 Uiso calc R 1 H H32B .3177 .8461 .8392 .158 Uiso calc R 1 H H32C .4913 .8783 .8555 .158 Uiso calc R 1 H O33 .42047(17) 1.03188(10) .81374(6) .0695(4) Uani d . 1 O O34 .01323(13) 1.34787(8) .47215(6) .0580(3) Uani d . 1 O C35 .1273(2) 1.41870(12) .45689(10) .0614(4) Uani d . 1 C H35A .0760 1.4720 .4348 .092 Uiso calc R 1 H H35B .2045 1.3940 .4239 .092 Uiso calc R 1 H H35C .1783 1.4377 .5016 .092 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 .0304(6) .0425(7) .0353(6) -.0017(5) .0017(5) -.0029(5) C2 .0331(6) .0421(7) .0371(6) .0012(5) .0029(5) .0016(5) C3 .0421(7) .0408(7) .0426(7) -.0027(5) .0075(5) -.0004(5) C4 .0412(7) .0479(8) .0397(7) .0053(6) .0058(5) -.0010(6) C5 .0386(7) .0522(8) .0424(7) .0042(6) .0092(5) .0083(6) C6 .0406(7) .0444(8) .0522(8) -.0037(6) .0045(6) .0070(6) C7 .0411(7) .0418(7) .0448(7) -.0014(6) .0034(6) -.0016(6) C8 .0331(6) .0432(7) .0307(6) .0001(5) .0028(5) -.0024(5) C9 .0311(6) .0512(8) .0465(7) -.0046(6) .0014(5) .0029(6) C10 .0319(6) .0584(9) .0517(8) .0031(6) -.0037(6) .0045(7) C11 .0437(7) .0475(8) .0356(6) .0045(6) .0001(5) .0019(5) C12 .0368(7) .0478(8) .0425(7) -.0042(6) .0040(5) .0031(6) C13 .0300(6) .0492(8) .0406(7) .0002(5) .0025(5) .0010(6) N18 .0324(5) .0432(6) .0336(5) .0015(4) -.0002(4) -.0025(4) C19 .0356(7) .0432(7) .0400(7) .0018(5) .0038(5) -.0004(5) C20 .0352(7) .0595(9) .0513(8) .0058(6) -.0002(6) -.0044(7) C21 .0361(7) .0546(8) .0502(8) -.0019(6) -.0033(6) -.0007(6) C22 .0391(7) .0415(7) .0383(7) -.0006(5) -.0035(5) -.0025(5) O23 .0693(7) .0593(7) .0478(6) -.0032(5) .0189(5) -.0102(5) C24 .0971(15) .0654(11) .0622(11) -.0137(10) .0195(10) -.0218(9) O25 .0548(6) .0706(8) .0520(6) .0025(5) .0201(5) .0133(5) C26 .1013(17) .117(2) .0619(12) .0127(15) .0163(11) .0370(12) O27 .0775(8) .0546(7) .0706(8) -.0223(6) .0196(6) .0025(6) C28 .0785(12) .0412(8) .0864(13) -.0104(8) -.0021(10) .0056(8) O29 .0417(5) .0682(7) .0527(6) -.0008(5) .0036(4) -.0217(5) C30 .0473(8) .0565(9) .0374(7) -.0016(6) -.0035(6) -.0021(6) O31 .1094(11) .0526(7) .0402(6) -.0051(6) .0004(6) .0082(5) C32 .188(3) .0769(15) .0511(11) -.0193(17) .0004(14) .0245(10) O33 .0889(9) .0815(9) .0381(6) .0027(7) -.0064(6) -.0116(6) O34 .0525(6) .0573(7) .0642(7) .0058(5) -.0023(5) .0183(5) C35 .0695(11) .0513(9) .0633(10) .0006(8) .0001(8) .0146(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 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 N18 C1 C8 112.08(10) ? N18 C1 C2 111.92(10) ? C8 C1 C2 113.02(10) ? N18 C1 H1 106.4 ? C8 C1 H1 106.4 ? C2 C1 H1 106.4 ? C7 C2 C3 120.29(12) ? C7 C2 C1 118.90(12) ? C3 C2 C1 120.80(12) ? C2 C3 C4 120.04(13) ? C2 C3 H3 120.0 ? C4 C3 H3 120.0 ? O23 C4 C5 115.79(12) ? O23 C4 C3 124.31(13) ? C5 C4 C3 119.89(13) ? O25 C5 C4 119.84(14) ? O25 C5 C6 120.16(14) ? C4 C5 C6 119.90(13) ? O27 C6 C7 124.50(14) ? O27 C6 C5 115.52(13) ? C7 C6 C5 119.98(13) ? C2 C7 C6 119.81(13) ? C2 C7 H7 120.1 ? C6 C7 H7 120.1 ? C13 C8 C9 117.36(12) ? C13 C8 C1 123.57(11) ? C9 C8 C1 118.93(11) ? C10 C9 C8 121.63(13) ? C10 C9 H9 119.2 ? C8 C9 H9 119.2 ? C9 C10 C11 120.20(13) ? C9 C10 H10 119.9 ? C11 C10 H10 119.9 ? O34 C11 C12 124.71(13) ? O34 C11 C10 116.21(13) ? C12 C11 C10 119.08(13) ? C11 C12 C13 119.95(13) ? C11 C12 H12 120.0 ? C13 C12 H12 120.0 ? C8 C13 C12 121.74(12) ? C8 C13 H13 119.1 ? C12 C13 H13 119.1 ? C19 N18 C22 113.70(10) yes C19 N18 C1 122.10(10) yes C22 N18 C1 124.20(10) yes O29 C19 N18 124.91(12) ? O29 C19 C20 127.06(12) ? N18 C19 C20 108.03(11) ? C19 C20 C21 104.21(11) ? C19 C20 H20A 110.9 ? C21 C20 H20A 110.9 ? C19 C20 H20B 110.9 ? C21 C20 H20B 110.9 ? H20A C20 H20B 108.9 ? C20 C21 C22 104.06(11) ? C20 C21 H21A 110.9 ? C22 C21 H21A 110.9 ? C20 C21 H21B 110.9 ? C22 C21 H21B 110.9 ? H21A C21 H21B 109.0 ? N18 C22 C30 114.40(11) ? N18 C22 C21 102.40(10) ? C30 C22 C21 110.23(12) ? N18 C22 H22 109.9 ? C30 C22 H22 109.9 ? C21 C22 H22 109.9 ? C4 O23 C24 118.13(12) ? O23 C24 H24A 109.5 ? O23 C24 H24B 109.5 ? H24A C24 H24B 109.5 ? O23 C24 H24C 109.5 ? H24A C24 H24C 109.5 ? H24B C24 H24C 109.5 ? C5 O25 C26 115.26(14) ? O25 C26 H26A 109.5 ? O25 C26 H26B 109.5 ? H26A C26 H26B 109.5 ? O25 C26 H26C 109.5 ? H26A C26 H26C 109.5 ? H26B C26 H26C 109.5 ? C6 O27 C28 117.98(13) ? O27 C28 H28A 109.5 ? O27 C28 H28B 109.5 ? H28A C28 H28B 109.5 ? O27 C28 H28C 109.5 ? H28A C28 H28C 109.5 ? H28B C28 H28C 109.5 ? O33 C30 O31 124.44(15) ? O33 C30 C22 122.90(15) ? O31 C30 C22 112.56(12) ? C30 O31 C32 115.06(15) ? O31 C32 H32A 109.5 ? O31 C32 H32B 109.5 ? H32A C32 H32B 109.5 ? O31 C32 H32C 109.5 ? H32A C32 H32C 109.5 ? H32B C32 H32C 109.5 ? C11 O34 C35 117.56(12) ? O34 C35 H35A 109.5 ? O34 C35 H35B 109.5 ? H35A C35 H35B 109.5 ? O34 C35 H35C 109.5 ? H35A C35 H35C 109.5 ? H35B C35 H35C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 N18 1.464(2) yes C1 C8 1.521(2) yes C1 C2 1.527(2) yes N18 C19 1.357(2) yes N18 C22 1.456(2) yes C19 C20 1.512(2) yes C20 C21 1.514(2) yes C21 C22 1.546(2) yes C1 H1 .9800 ? C2 C7 1.386(2) ? C2 C3 1.390(2) ? C3 C4 1.392(2) ? C3 H3 .9300 ? C4 O23 1.367(2) ? C4 C5 1.388(2) ? C5 O25 1.378(2) ? C5 C6 1.398(2) ? C6 O27 1.363(2) ? C6 C7 1.393(2) ? C7 H7 .9300 ? C8 C13 1.380(2) ? C8 C9 1.399(2) ? C9 C10 1.377(2) ? C9 H9 .9300 ? C10 C11 1.391(2) ? C10 H10 .9300 ? C11 O34 1.363(2) ? C11 C12 1.385(2) ? C12 C13 1.392(2) ? C12 H12 .9300 ? C13 H13 .9300 ? C19 O29 1.223(2) ? C20 H20A .9700 ? C20 H20B .9700 ? C21 H21A .9700 ? C21 H21B .9700 ? C22 C30 1.517(2) ? C22 H22 .9800 ? O23 C24 1.417(2) ? C24 H24A .9600 ? C24 H24B .9600 ? C24 H24C .9600 ? O25 C26 1.410(2) ? C26 H26A .9600 ? C26 H26B .9600 ? C26 H26C .9600 ? O27 C28 1.412(2) ? C28 H28A .9600 ? C28 H28B .9600 ? C28 H28C .9600 ? C30 O33 1.203(2) ? C30 O31 1.316(2) ? O31 C32 1.449(2) ? C32 H32A .9600 ? C32 H32B .9600 ? C32 H32C .9600 ? O34 C35 1.425(2) ? C35 H35A .9600 ? C35 H35B .9600 ? C35 H35C .9600 ? 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 N18 C1 C2 C7 -100.44(14) ? C8 C1 C2 C7 131.88(13) ? N18 C1 C2 C3 78.68(16) ? C8 C1 C2 C3 -49.0(2) yes C7 C2 C3 C4 2.1(2) ? C1 C2 C3 C4 -177.03(12) ? C2 C3 C4 O23 177.82(13) ? C2 C3 C4 C5 -3.5(2) ? O23 C4 C5 O25 4.8(2) ? C3 C4 C5 O25 -173.98(13) ? O23 C4 C5 C6 -178.83(13) ? C3 C4 C5 C6 2.4(2) ? O25 C5 C6 O27 -2.8(2) ? C4 C5 C6 O27 -179.17(13) ? O25 C5 C6 C7 176.54(13) ? C4 C5 C6 C7 .2(2) ? C3 C2 C7 C6 .5(2) ? C1 C2 C7 C6 179.62(12) ? O27 C6 C7 C2 177.66(14) ? C5 C6 C7 C2 -1.6(2) ? N18 C1 C8 C13 3.62(17) ? C2 C1 C8 C13 131.21(13) ? N18 C1 C8 C9 179.25(11) ? C2 C1 C8 C9 -53.16(16) ? C13 C8 C9 C10 -1.4(2) ? C1 C8 C9 C10 -177.33(13) ? C8 C9 C10 C11 -.4(2) ? C9 C10 C11 O34 -178.44(13) ? C9 C10 C11 C12 1.8(2) ? O34 C11 C12 C13 178.88(13) ? C10 C11 C12 C13 -1.3(2) ? C9 C8 C13 C12 1.9(2) ? C1 C8 C13 C12 177.56(12) ? C11 C12 C13 C8 -.5(2) ? C8 C1 N18 C19 -102.61(14) ? C2 C1 N18 C19 129.20(10) yes C8 C1 N18 C22 76.66(15) ? C2 C1 N18 C22 -51.51(16) ? C22 N18 C19 O29 177.95(14) ? C1 N18 C19 O29 -2.7(2) ? C22 N18 C19 C20 -2.09(16) ? C1 N18 C19 C20 177.25(12) ? O29 C19 C20 C21 164.46(15) ? N18 C19 C20 C21 -15.50(16) ? C19 C20 C21 C22 25.71(15) ? C19 N18 C22 C30 -100.98(14) ? C1 N18 C22 C30 79.70(16) ? C19 N18 C22 C21 18.27(15) ? C1 N18 C22 C21 -161.05(12) ? C20 C21 C22 N18 -26.49(14) ? C20 C21 C22 C30 95.64(14) ? C5 C4 O23 C24 168.4(2) yes C3 C4 O23 C24 -12.9(2) ? C4 C5 O25 C26 -95.7(2) ? C6 C5 O25 C26 87.9(2) yes C7 C6 O27 C28 -.8(2) yes C5 C6 O27 C28 178.52(15) ? N18 C22 C30 O33 -144.00(15) ? C21 C22 C30 O33 101.26(18) ? N18 C22 C30 O31 39.48(18) ? C21 C22 C30 O31 -75.26(16) ? O33 C30 O31 C32 -1.3(3) ? C22 C30 O31 C32 175.18(19) ? C12 C11 O34 C35 -4.6(2) ? C10 C11 O34 C35 175.60(14) ?