#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006347.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_2006347 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1997 _journal_volume 53 _journal_page_first 913 _journal_page_last 915 _publ_section_title ; (4RS,1'RS)-Methyl 1-Phenyl-2-piperidinoethyl 1,4-Dihydro-2,6-dimethyl-4-(2- thienyl)pyridine-3,5-dicarboxylate Methanol Solvate, C~27~H~32~N~2~O~4~S.1.5(CH~4~O) ; loop_ _publ_author_name 'Marubayashi, Nobuhiro' 'Mishina, Tadashi' 'Hamasaki, Toshio' 'Hirayama, Noriaki' _chemical_formula_moiety 'C27 H32 N2 O4 S, 1.5(C H4 O)' _chemical_formula_sum 'C28.5 H38 N2 O5.5 S' _chemical_formula_weight 528.68 _symmetry_cell_setting triclinic _symmetry_space_group_name_h-m 'P -1' _cell_length_a 14.074(2) _cell_length_b 15.738(2) _cell_length_c 13.588(2) _cell_angle_alpha 96.820(10) _cell_angle_beta 100.610(10) _cell_angle_gamma 74.630(10) _cell_volume 2844.5(7) _cell_formula_units_z 4 _cell_measurement_temperature 294 _exptl_crystal_density_diffrn 1.23 _diffrn_ambient_temperature 294 _refine_ls_R_factor_obs .049 _refine_ls_wR_factor_obs .070 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 S'A .56287(6) .34414(5) .49337(7) .0661(2) Uani ? S''A .61180(10) .26560(10) .66870(10) .0772(5) Uani ? O1A .28260(10) .23890(10) .43000(10) .0637(5) Uani ? O2A .41260(10) .25250(10) .36750(10) .0620(5) Uani ? O3A .80370(10) .01460(10) .57750(10) .0528(4) Uani ? O4A .73980(10) .10381(9) .45160(10) .0457(4) Uani ? N1A .50270(10) .07180(10) .63450(10) .0428(5) Uani ? N2A .78420(10) .02510(10) .24790(10) .0540(5) Uani ? C2A .42710(10) .12500(10) .5730(2) .0401(6) Uani ? C3A .44980(10) .16790(10) .50350(10) .0386(5) Uani ? C4A .55760(10) .16750(10) .50200(10) .0371(5) Uani ? C5A .62920(10) .08920(10) .55250(10) .0354(5) Uani ? C6A .60070(10) .04860(10) .62000(10) .0370(5) Uani ? C7A .3250(2) .1289(2) .5928(2) .0559(7) Uani ? C8A .3719(2) .22180(10) .4335(2) .0443(6) Uani ? C9A .6661(2) -.02140(10) .6857(2) .0468(6) Uani ? C10A .73200(10) .06400(10) .53220(10) .0382(5) Uani ? C11A .57920(10) .25280(10) .5543(2) .0418(6) Uani ? C13A .6235(2) .3589(2) .6777(2) .0725(9) Uani ? C14A .6006(2) .4020(2) .5948(3) .0765(9) Uani ? C15A .3467(2) .3136(2) .2994(2) .0860(10) Uani ? C16A .8377(2) .08900(10) .4244(2) .0495(6) Uani ? C17A .8218(2) .0951(2) .3116(2) .0543(7) Uani ? C18A .8919(2) .1564(2) .4783(2) .0513(6) Uani ? C19A .8462(2) .2307(2) .5326(2) .0669(8) Uani ? C20A .8977(2) .2919(2) .5778(2) .0840(10) Uani ? C21A .9951(2) .2814(2) .5681(3) .0900(10) Uani ? C22A 1.0419(2) .2085(2) .5139(3) .0890(10) Uani ? C23A .9916(2) .1452(2) .4694(2) .0715(9) Uani ? C24A .7775(2) .0444(2) .1432(2) .0736(8) Uani ? C25A .7435(2) -.0252(2) .0691(2) .0890(10) Uani ? C26A .8119(2) -.1161(2) .0864(3) .0990(10) Uani ? C27A .8215(3) -.1344(2) .1939(3) .0900(10) Uani ? C28A .8532(2) -.0622(2) .2662(2) .0721(9) Uani ? S'B .08601(9) .86148(7) .00770(10) .0745(3) Uani ? S''B .13016(9) .78439(7) .18411(8) .0683(3) Uani ? O1B -.17000(10) .70490(10) -.09430(10) .0704(6) Uani ? O2B -.05390(10) .76370(10) -.12870(10) .0604(5) Uani ? O3B .35240(10) .53430(10) .07830(10) .0674(5) Uani ? O4B .29050(10) .63286(9) -.03750(10) .0440(4) Uani ? N1B .05560(10) .57800(10) .13490(10) .0486(5) Uani ? N2B .33150(10) .54880(10) -.22930(10) .0528(5) Uani ? C2B -.0227(2) .62190(10) .0681(2) .0448(6) Uani ? C3B -.00430(10) .66830(10) -.0004(2) .0413(6) Uani ? C4B .09970(10) .68240(10) .00630(10) .0383(5) Uani ? C5B .17820(10) .60650(10) .05570(10) .0376(5) Uani ? C6B .1538(2) .56150(10) .1219(2) .0409(6) Uani ? C7B -.1215(2) .6107(2) .0832(2) .0619(7) Uani ? C8B -.0845(2) .71140(10) -.0769(2) .0474(6) Uani ? C9B .2212(2) .49110(10) .1855(2) .0537(7) Uani ? C10B .28090(10) .58610(10) .0360(2) .0411(6) Uani ? C11B .10770(10) .77050(10) .0622(2) .0427(6) Uani ? C13B .1285(2) .8850(2) .1900(2) .0802(9) Uani ? C14B .1077(2) .9217(2) .1031(3) .0830(10) Uani ? C15B -.1281(2) .8135(2) -.2020(2) .0800(10) Uani ? C16B .3898(2) .61990(10) -.0605(2) .0469(6) Uani ? C17B .3820(2) .6146(2) -.1742(2) .0563(7) Uani ? C18B .4361(2) .6937(2) -.0102(2) .0495(6) Uani ? C19B .3845(2) .7656(2) .0433(2) .0661(8) Uani ? C20B .4296(2) .8308(2) .0890(2) .0840(10) Uani ? C21B .5269(2) .8261(2) .0815(2) .0820(10) Uani ? C22B .5789(2) .7557(2) .0277(3) .0820(10) Uani ? C23B .5341(2) .6896(2) -.0176(2) .0670(8) Uani ? C24B .3362(2) .5482(2) -.3370(2) .0690(8) Uani ? C25B .2803(2) .4859(2) -.4005(2) .0830(10) Uani ? C26B .3199(3) .3930(2) -.3660(3) .0930(10) Uani ? C27B .3204(3) .3945(2) -.2538(2) .0860(10) Uani ? C28B .3752(2) .4594(2) -.1954(2) .0681(8) Uani ? O(M1) .87300(10) .38740(10) .23560(10) .0632(5) Uani ? C(M1) .8909(3) .3067(2) .2782(2) .0890(10) Uani ? O(M2) .57380(10) .03590(10) .24830(10) .0758(6) Uani ? C(M2) .5210(3) .1029(2) .1859(3) .1010(10) Uani ? O(M3) .0131(2) .47870(10) .2815(2) .1109(7) Uani ? C(M3) .0639(3) .4545(3) .3737(3) .1110(10) Uani ? HN1A .4852 .0399 .6784 .0580 Uiso calc HC4A .5671 .1626 .4327 .0506 Uiso calc H1C7A .2750 .1666 .5489 .0760 Uiso calc H2C7A .3125 .0714 .5839 .0760 Uiso calc H3C7A .3183 .1517 .6607 .0760 Uiso calc H1C9A .7336 -.0353 .6727 .0660 Uiso calc H2C9A .6665 -.0021 .7548 .0660 Uiso calc H3C9A .6433 -.0745 .6729 .0660 Uiso calc HC13A .6487 .3852 .7427 .0974 Uiso calc HC14A .6081 .4614 .5977 .1025 Uiso calc H1C15A .3827 .3324 .2562 .1162 Uiso calc H2C15A .2968 .2882 .2592 .1162 Uiso calc H3C15A .3132 .3661 .3363 .1162 Uiso calc HC16A .8772 .0312 .4427 .0675 Uiso calc H1C17A .7755 .1516 .2971 .0739 Uiso calc H2C17A .8842 .0971 .2934 .0739 Uiso calc HC19A .7767 .2386 .5397 .0888 Uiso calc HC20A .8639 .3442 .6170 .1133 Uiso calc HC21A 1.0318 .3245 .6000 .1207 Uiso calc HC22A 1.1108 .2013 .5068 .1190 Uiso calc HC23A 1.0256 .0920 .4319 .0969 Uiso calc H1C24A .8410 .0495 .1313 .1011 Uiso calc H2C24A .7311 .1023 .1314 .1011 Uiso calc H1C25A .7392 -.0111 .0011 .1186 Uiso calc H2C25A .6762 -.0261 .0769 .1186 Uiso calc H1C26A .8761 -.1173 .0710 .1257 Uiso calc H2C26A .7864 -.1603 .0417 .1257 Uiso calc H1C27A .8675 -.1907 .2063 .1172 Uiso calc H2C27A .7571 -.1392 .2061 .1172 Uiso calc H1C28A .8568 -.0752 .3352 .0974 Uiso calc H2C28A .9201 -.0607 .2595 .0974 Uiso calc HN1B .0420 .5437 .1847 .0647 Uiso calc HC4B .1117 .6840 -.0611 .0528 Uiso calc H1C7B -.1747 .6427 .0360 .0850 Uiso calc H2C7B -.1233 .5502 .0748 .0850 Uiso calc H3C7B -.1350 .6334 .1494 .0850 Uiso calc H1C9B .2887 .4817 .1749 .0752 Uiso calc H2C9B .2187 .5082 .2550 .0752 Uiso calc H3C9B .2016 .4369 .1691 .0752 Uiso calc HC13B .1418 .9176 .2545 .1061 Uiso calc HC14B .1064 .9830 .0993 .1121 Uiso calc H1C15B -.0997 .8493 -.2349 .1073 Uiso calc H2C15B -.1570 .7755 -.2515 .1073 Uiso calc H3C15B -.1809 .8526 -.1703 .1073 Uiso calc HC16B .4323 .5642 -.0366 .0653 Uiso calc H1C17B .3463 .6727 -.1961 .0773 Uiso calc H2C17B .4481 .6032 -.1911 .0773 Uiso calc HC19B .3149 .7695 .0482 .0895 Uiso calc HC20B .3928 .8817 .1272 .1138 Uiso calc HC21B .5594 .8719 .1137 .1101 Uiso calc HC22B .6470 .7534 .0198 .1095 Uiso calc HC23B .5724 .6380 -.0539 .0906 Uiso calc H1C24B .4054 .5312 -.3466 .0956 Uiso calc H2C24B .3095 .6078 -.3583 .0956 Uiso calc H1C25B .2854 .4850 -.4704 .1120 Uiso calc H2C25B .2103 .5054 -.3953 .1120 Uiso calc H1C26B .3872 .3699 -.3792 .1222 Uiso calc H2C26B .2806 .3543 -.4026 .1222 Uiso calc H1C27B .3480 .3359 -.2315 .1136 Uiso calc H2C27B .2515 .4118 -.2420 .1136 Uiso calc H1C28B .3752 .4593 -.1243 .0913 Uiso calc H2C28B .4451 .4402 -.2043 .0913 Uiso calc H1(M1) .7974 .4142 .2258 .0835 Uiso calc H2(M1) .9604 .2784 .2888 .1154 Uiso calc H3(M1) .8672 .3145 .3411 .1154 Uiso calc H4(M1) .8569 .2669 .2345 .1154 Uiso calc H1(M2) .6457 .0352 .2530 .0986 Uiso calc H2(M2) .4509 .1073 .1775 .1266 Uiso calc H3(M2) .5327 .1589 .2129 .1266 Uiso calc H4(M2) .5407 .0911 .1204 .1266 Uiso calc H1(M3) -.0397 .4454 .2551 .1403 Uiso calc H2(M3) .1132 .4868 .3977 .1407 Uiso calc H3(M3) .0196 .4643 .4226 .1407 Uiso calc H4(M3) .0972 .3923 .3712 .1407 Uiso calc 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 S'A .0713(4) .0516(4) .0814(5) -.0214(3) .0061(4) .0237(3) S''A .0718(8) .0680(8) .0870(10) -.0251(6) -.0023(8) -.0072(7) O1A .0379(8) .0690(10) .0740(10) -.0011(7) -.0052(8) .0138(9) O2A .0508(8) .0718(9) .0586(9) -.0047(7) -.0069(7) .0341(7) O3A .0374(7) .0575(8) .0591(8) .0030(6) .0073(6) .0212(7) O4A .0364(6) .0514(7) .0496(7) -.0024(6) .0122(6) .0167(6) N1A .0384(8) .0485(9) .0425(8) -.0073(7) .0084(7) .0126(7) N2A .0603(9) .0520(10) .0560(10) -.0144(8) .0249(8) .0061(8) C2A .0356(9) .0410(10) .0410(10) -.0066(8) .0046(8) .0008(9) C3A .0350(9) .0380(10) .0390(10) -.0057(8) .0018(8) .0027(8) C4A .0371(9) .0378(9) .0349(9) -.0054(8) .0056(8) .0066(8) C5A .0337(9) .0354(9) .0348(9) -.0057(7) .0027(8) .0042(8) C6A .0365(9) .0369(9) .0360(9) -.0073(7) .0035(8) .0038(8) C7A .0390(10) .0600(10) .0700(10) -.0083(9) .0150(10) .0100(10) C8A .0410(10) .0390(10) .0460(10) -.0066(8) -.0021(9) .0010(9) C9A .0470(10) .0450(10) .0490(10) -.0070(9) .0061(9) .0158(9) C10A .0390(9) .0338(9) .0410(10) -.0074(7) .0070(8) .0040(8) C11A .0321(9) .0390(10) .0550(10) -.0055(8) .0093(8) .0098(9) C13A .0710(10) .0700(10) .081(2) -.0320(10) .0110(10) -.0110(10) C14A .0700(10) .0450(10) .119(2) -.0210(10) .0160(10) .0090(10) C15A .076(2) .090(2) .083(2) -.0060(10) -.0200(10) .0500(10) C16A .0390(10) .0510(10) .0580(10) -.0010(9) .0176(9) .0140(10) C17A .0570(10) .0550(10) .0580(10) -.0153(9) .0208(9) .0090(10) C18A .0370(10) .0610(10) .0550(10) -.0047(9) .0069(9) .0190(10) C19A .0570(10) .0750(10) .075(2) -.0240(10) .0210(10) .0010(10) C20A .086(2) .090(2) .085(2) -.0420(10) .0180(10) -.005(2) C21A .081(2) .110(2) .085(2) -.0470(10) -.009(2) .016(2) C22A .0420(10) .123(2) .106(2) -.0270(10) -.0110(10) .038(2) C23A .0390(10) .088(2) .083(2) -.0040(10) .0040(10) .0260(10) C24A .096(2) .081(2) .0570(10) -.0330(10) .0310(10) .0060(10) C25A .116(2) .105(2) .0600(10) -.046(2) .0340(10) -.0120(10) C26A .107(2) .096(2) .107(2) -.037(2) .0620(10) -.036(2) C27A .102(2) .061(2) .111(2) -.0180(10) .044(2) -.015(2) C28A .0690(10) .0570(10) .090(2) -.0070(10) .0280(10) .0000(10) S'B .0861(6) .0549(5) .0912(7) -.0278(4) .0140(5) .0164(5) S''B .0794(6) .0591(5) .0605(6) -.0206(5) -.0055(5) -.0002(5) O1B .0479(8) .0800(10) .0790(10) -.0232(7) -.0157(8) .0111(9) O2B .0511(8) .0679(9) .0572(9) -.0108(7) -.0105(7) .0244(7) O3B .0469(8) .0770(10) .0739(9) .0082(8) .0121(7) .0376(8) O4B .0365(6) .0502(7) .0458(7) -.0069(6) .0061(6) .0148(6) N1B .0473(9) .0543(9) .0492(9) -.0178(7) .0053(7) .0153(8) N2B .0574(9) .0590(10) .0474(9) -.0176(8) .0195(7) .0007(8) C2B .0410(10) .0460(10) .0480(10) -.0147(8) .0051(9) .0000(9) C3B .0390(10) .0400(10) .0420(10) -.0094(8) .0026(8) -.0004(9) C4B .0394(9) .0400(10) .0348(9) -.0085(8) .0040(8) .0069(8) C5B .0396(9) .0356(9) .0360(10) -.0082(7) .0027(8) .0048(8) C6B .0440(10) .0379(9) .0410(10) -.0115(8) .0025(8) .0055(8) C7B .0480(10) .0720(10) .072(2) -.0240(10) .0090(10) .0080(10) C8B .0440(10) .0440(10) .0470(10) -.0094(9) -.0030(10) -.0030(10) C9B .0560(10) .0490(10) .0580(10) -.0161(9) -.0010(10) .0227(9) C10B .0410(10) .0390(10) .0400(10) -.0065(8) .0025(8) .0065(9) C11B .0326(9) .0430(10) .0530(10) -.0083(8) .0059(8) .0075(9) C13B .0710(10) .080(2) .086(2) -.0310(10) .0050(10) -.024(2) C14B .073(2) .0480(10) .129(3) -.0220(10) .008(2) .0140(10) C15B .069(2) .086(2) .073(2) -.0060(10) -.0200(10) .0340(10) C16B .0366(9) .0520(10) .0520(10) -.0069(8) .0109(9) .0090(10) C17B .0550(10) .0640(10) .0570(10) -.0226(9) .0159(9) .0060(10) C18B .0420(10) .0550(10) .0500(10) -.0110(9) .0017(9) .0120(10) C19B .0580(10) .0690(10) .073(2) -.0200(10) .0140(10) -.0040(10) C20B .090(2) .079(2) .085(2) -.0350(10) .014(2) -.014(2) C21B .085(2) .082(2) .083(2) -.0430(10) -.012(2) .0110(10) C22B .0540(10) .092(2) .104(2) -.0320(10) -.0060(10) .021(2) C23B .0440(10) .0730(10) .084(2) -.0140(10) .0040(10) .0130(10) C24B .0740(10) .090(2) .0490(10) -.0250(10) .0230(10) .0010(10) C25B .089(2) .110(2) .0540(10) -.034(2) .0230(10) -.017(2) C26B .101(2) .089(2) .090(2) -.030(2) .034(2) -.032(2) C27B .113(2) .0600(10) .089(2) -.0270(10) .031(2) -.0100(10) C28B .079(2) .0580(10) .0670(10) -.0100(10) .0210(10) .0020(10) O(M1) .0583(9) .0693(9) .0632(9) -.0170(7) .0075(8) .0103(8) C(M1) .096(2) .086(2) .086(2) -.005(2) .024(2) .0310(10) O(M2) .0662(9) .0890(10) .0820(10) -.0192(8) .0154(8) .0373(8) C(M2) .092(2) .109(2) .104(2) .002(2) .029(2) .052(2) O(M3) .1020(10) .1580(10) .1020(10) -.0788(8) -.0150(10) .0670(10) C(M3) .118(2) .144(3) .085(2) -.062(2) -.001(2) .029(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S'A C11A 1.686(2) no S'A C14A 1.643(3) no S''A C11A 1.543(3) no S''A C13A 1.508(3) no O1A C8A 1.207(3) yes O2A C8A 1.343(3) yes O2A C15A 1.437(3) yes O3A C10A 1.213(2) yes O4A C10A 1.359(3) yes O4A C16A 1.444(3) yes N1A C2A 1.379(2) yes N1A C6A 1.375(3) yes N2A C17A 1.468(3) yes N2A C24A 1.471(3) yes N2A C28A 1.476(3) yes C2A C3A 1.350(3) no C2A C7A 1.494(3) no C3A C4A 1.520(3) no C3A C8A 1.464(3) no C4A C5A 1.514(2) no C4A C11A 1.520(3) no C5A C6A 1.350(3) no C5A C10A 1.465(3) no C6A C9A 1.500(3) no C13A C14A 1.328(5) no C16A C17A 1.518(3) no C16A C18A 1.511(3) no C18A C19A 1.377(3) no C18A C23A 1.392(4) no C19A C20A 1.377(4) no C20A C21A 1.366(5) no C21A C22A 1.367(4) no C22A C23A 1.391(5) no C24A C25A 1.511(4) no C25A C26A 1.515(4) no C26A C27A 1.497(5) no C27A C28A 1.516(4) no S'B C11B 1.621(3) no S'B C14B 1.546(3) no S''B C11B 1.628(2) no S''B C13B 1.571(3) no O1B C8B 1.211(3) yes O2B C8B 1.340(3) yes O2B C15B 1.437(3) yes O3B C10B 1.213(2) yes O4B C10B 1.355(3) yes O4B C16B 1.445(3) yes N1B C2B 1.376(2) yes N1B C6B 1.378(3) yes N2B C17B 1.464(3) yes N2B C24B 1.476(3) yes N2B C28B 1.470(3) yes C2B C3B 1.349(3) no C2B C7B 1.500(4) no C3B C4B 1.522(3) no C3B C8B 1.464(3) no C4B C5B 1.522(2) no C4B C11B 1.521(3) no C5B C6B 1.349(3) no C5B C10B 1.463(3) no C6B C9B 1.497(3) no C13B C14B 1.325(5) no C16B C17B 1.522(3) no C16B C18B 1.514(3) no C18B C19B 1.378(3) no C18B C23B 1.385(4) no C19B C20B 1.375(4) no C20B C21B 1.373(5) no C21B C22B 1.368(4) no C22B C23B 1.383(4) no C24B C25B 1.511(5) no C25B C26B 1.518(5) no C26B C27B 1.520(5) no C27B C28B 1.505(4) no O(M1) C(M1) 1.402(4) no O(M2) C(M2) 1.396(4) no O(M3) C(M3) 1.366(4) no _cod_database_code 2006347