#------------------------------------------------------------------------------ #$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011077.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_2011077 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 878 _journal_page_last 880 _publ_section_title ; Tetrabutylammonium \a-acetyl-\g-butyrolactonate contains a three-dimensional hydrogen-bonded network ; loop_ _publ_author_name 'Goddard, Richard' 'H\"utte, Stephan' 'Reetz, Manfred T.' _chemical_formula_moiety 'C16 H36 N +, C6 H7 O3 -' _chemical_formula_sum 'C22 H43 N O3' _chemical_formula_weight 369.57 _chemical_melting_point 428 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.309(4) _cell_length_b 13.659(3) _cell_length_c 13.6110(10) _cell_angle_alpha 89.920(10) _cell_angle_beta 94.100(10) _cell_angle_gamma 95.01(2) _cell_volume 2273.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _exptl_crystal_density_diffrn 1.080 _diffrn_ambient_temperature 100 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .49742(15) -.36096(15) -.36924(14) .0339(5) Uani d . 1 . . O O2 .50227(15) -.13762(15) -.13849(13) .0322(4) Uani d . 1 . . O O3 .51419(18) -.03879(15) -.26826(15) .0390(5) Uani d . 1 . . O O4 -.01567(16) -.37392(16) .35216(16) .0395(5) Uani d . 1 . . O O5 .00909(15) -.14199(13) .13132(15) .0315(4) Uani d . 1 . . O O6 .02016(18) -.27096(16) .03429(16) .0417(5) Uani d . 1 . . O N1 -.25003(15) .48491(13) -.47121(13) .0148(4) Uani d . 1 . . N N2 .24988(15) .01817(14) .96618(13) .0168(4) Uani d . 1 . . N C1 -.31881(18) .39637(16) -.43582(16) .0167(4) Uani d . 1 . . C H1A -.3655 .3690 -.4913 .020 Uiso calc R 1 . . H H1B -.3659 .4184 -.3877 .020 Uiso calc R 1 . . H C2 -.25583(19) .31531(17) -.39008(17) .0200(5) Uani d . 1 . . C H2A -.2023 .3427 -.3395 .024 Uiso calc R 1 . . H H2B -.2172 .2850 -.4400 .024 Uiso calc R 1 . . H C3 -.3343(2) .23811(17) -.34490(18) .0225(5) Uani d . 1 . . C H3A -.3697 .2682 -.2926 .027 Uiso calc R 1 . . H H3B -.3906 .2143 -.3948 .027 Uiso calc R 1 . . H C4 -.2761(2) .15211(18) -.3035(2) .0284(6) Uani d . 1 . . C H4A -.3278 .1058 -.2750 .043 Uiso calc R 1 . . H H4B -.2205 .1753 -.2539 .043 Uiso calc R 1 . . H H4C -.2431 .1208 -.3555 .043 Uiso calc R 1 . . H C5 -.33182(18) .55141(16) -.51783(16) .0172(4) Uani d . 1 . . C H5A -.3723 .5163 -.5726 .021 Uiso calc R 1 . . H H5B -.3837 .5634 -.4697 .021 Uiso calc R 1 . . H C6 -.28552(19) .64984(17) -.55504(18) .0210(5) Uani d . 1 . . C H6A -.2297 .6404 -.6000 .025 Uiso calc R 1 . . H H6B -.2525 .6901 -.5003 .025 Uiso calc R 1 . . H C7 -.3783(2) .70060(18) -.60775(18) .0237(5) Uani d . 1 . . C H7A -.4062 .6624 -.6656 .028 Uiso calc R 1 . . H H7B -.4373 .7024 -.5644 .028 Uiso calc R 1 . . H C8 -.3430(2) .80474(19) -.6390(2) .0304(6) Uani d . 1 . . C H8A -.4038 .8328 -.6731 .046 Uiso calc R 1 . . H H8B -.2845 .8035 -.6819 .046 Uiso calc R 1 . . H H8C -.3184 .8438 -.5818 .046 Uiso calc R 1 . . H C9 -.16980(18) .45642(17) -.54346(16) .0172(4) Uani d . 1 . . C H9A -.1247 .5151 -.5600 .021 Uiso calc R 1 . . H H9B -.1220 .4119 -.5106 .021 Uiso calc R 1 . . H C10 -.21943(19) .40820(18) -.63835(16) .0213(5) Uani d . 1 . . C H10A -.2588 .4549 -.6774 .026 Uiso calc R 1 . . H H10B -.2706 .3529 -.6237 .026 Uiso calc R 1 . . H C11 -.1280(2) .37318(19) -.69558(18) .0249(5) Uani d . 1 . . C H11A -.0723 .4272 -.7018 .030 Uiso calc R 1 . . H H11B -.0947 .3212 -.6590 .030 Uiso calc R 1 . . H C12 -.1690(2) .3352(2) -.79786(19) .0334(6) Uani d . 1 . . C H12A -.1090 .3136 -.8310 .050 Uiso calc R 1 . . H H12B -.2004 .3869 -.8349 .050 Uiso calc R 1 . . H H12C -.2235 .2811 -.7921 .050 Uiso calc R 1 . . H C13 -.17959(18) .53591(16) -.38701(16) .0172(4) Uani d . 1 . . C H13A -.1249 .4927 -.3638 .021 Uiso calc R 1 . . H H13B -.1413 .5945 -.4125 .021 Uiso calc R 1 . . H C14 -.2395(2) .56520(18) -.29993(17) .0217(5) Uani d . 1 . . C H14A -.2687 .5068 -.2668 .026 Uiso calc R 1 . . H H14B -.3000 .6024 -.3225 .026 Uiso calc R 1 . . H C15 -.1610(2) .62760(19) -.22839(18) .0254(5) Uani d . 1 . . C H15A -.0988 .5911 -.2089 .030 Uiso calc R 1 . . H H15B -.1340 .6868 -.2616 .030 Uiso calc R 1 . . H C16 -.2147(3) .6558(2) -.1375(2) .0384(7) Uani d . 1 . . C H16A -.1629 .6955 -.0951 .058 Uiso calc R 1 . . H H16B -.2394 .5975 -.1033 .058 Uiso calc R 1 . . H H16C -.2759 .6924 -.1564 .058 Uiso calc R 1 . . H C17 .17103(19) .03625(17) 1.04401(16) .0188(5) Uani d . 1 . . C H17A .1231 .0847 1.0189 .023 Uiso calc R 1 . . H H17B .1259 -.0244 1.0536 .023 Uiso calc R 1 . . H C18 .2233(2) .07132(18) 1.14320(17) .0221(5) Uani d . 1 . . C H18A .2692 .1318 1.1353 .027 Uiso calc R 1 . . H H18B .2689 .0224 1.1712 .027 Uiso calc R 1 . . H C19 .1341(2) .08878(19) 1.21214(18) .0267(5) Uani d . 1 . . C H19A .0918 .1407 1.1857 .032 Uiso calc R 1 . . H H19B .0850 .0295 1.2153 .032 Uiso calc R 1 . . H C20 .1814(3) .1171(2) 1.3154(2) .0356(6) Uani d . 1 . . C H20A .1231 .1276 1.3563 .053 Uiso calc R 1 . . H H20B .2291 .1763 1.3126 .053 Uiso calc R 1 . . H H20C .2219 .0652 1.3424 .053 Uiso calc R 1 . . H C21 .17774(19) -.01864(17) .87630(16) .0193(5) Uani d . 1 . . C H21A .1280 .0307 .8582 .023 Uiso calc R 1 . . H H21B .1338 -.0774 .8946 .023 Uiso calc R 1 . . H C22 .2368(2) -.04243(18) .78587(17) .0229(5) Uani d . 1 . . C H22A .2794 .0159 .7647 .027 Uiso calc R 1 . . H H22B .2863 -.0926 .8018 .027 Uiso calc R 1 . . H C23 .1527(2) -.0789(2) .70363(19) .0319(6) Uani d . 1 . . C H23A .1095 -.1362 .7262 .038 Uiso calc R 1 . . H H23B .1037 -.0282 .6884 .038 Uiso calc R 1 . . H C24 .2052(3) -.1054(3) .6108(2) .0457(8) Uani d . 1 . . C H24A .1493 -.1278 .5611 .069 Uiso calc R 1 . . H H24B .2526 -.1566 .6251 .069 Uiso calc R 1 . . H H24C .2470 -.0485 .5874 .069 Uiso calc R 1 . . H C25 .32915(18) -.05611(17) 1.00083(16) .0184(5) Uani d . 1 . . C H25A .3801 -.0622 .9504 .022 Uiso calc R 1 . . H H25B .3710 -.0302 1.0596 .022 Uiso calc R 1 . . H C26 .2786(2) -.15765(17) 1.02362(18) .0224(5) Uani d . 1 . . C H26A .2413 -.1875 .9644 .027 Uiso calc R 1 . . H H26B .2254 -.1533 1.0724 .027 Uiso calc R 1 . . H C27 .3686(2) -.22050(18) 1.06299(19) .0260(5) Uani d . 1 . . C H27A .4243 -.2198 1.0159 .031 Uiso calc R 1 . . H H27B .4026 -.1918 1.1240 .031 Uiso calc R 1 . . H C28 .3263(3) -.3265(2) 1.0816(2) .0351(6) Uani d . 1 . . C H28A .3857 -.3625 1.1068 .053 Uiso calc R 1 . . H H28B .2947 -.3560 1.0210 .053 Uiso calc R 1 . . H H28C .2717 -.3278 1.1287 .053 Uiso calc R 1 . . H C29 .32066(18) .11107(17) .94416(17) .0185(5) Uani d . 1 . . C H29A .3660 .1303 1.0034 .022 Uiso calc R 1 . . H H29B .3691 .0957 .8943 .022 Uiso calc R 1 . . H C30 .26102(19) .19837(17) .90925(17) .0199(5) Uani d . 1 . . C H30A .2105 .2142 .9572 .024 Uiso calc R 1 . . H H30B .2194 .1826 .8472 .024 Uiso calc R 1 . . H C31 .3441(2) .28674(18) .89582(19) .0243(5) Uani d . 1 . . C H31A .3852 .3020 .9582 .029 Uiso calc R 1 . . H H31B .3953 .2696 .8490 .029 Uiso calc R 1 . . H C32 .2901(2) .37753(19) .8593(2) .0317(6) Uani d . 1 . . C H32A .3451 .4311 .8531 .048 Uiso calc R 1 . . H H32B .2395 .3950 .9054 .048 Uiso calc R 1 . . H H32C .2517 .3637 .7963 .048 Uiso calc R 1 . . H C33 .4833(2) -.3546(2) -.1960(2) .0363(6) Uani d . 1 . . C H33A .4077 -.3755 -.1892 .054 Uiso calc R 1 . . H H33B .5091 -.3086 -.1444 .054 Uiso calc R 1 . . H H33C .5254 -.4106 -.1914 .054 Uiso calc R 1 . . H C34 .49556(19) -.3053(2) -.29612(19) .0272(6) Uani d . 1 . . C C35 .5024(2) -.2038(2) -.30395(18) .0271(5) Uani d . 1 . . C C36 .5125(3) -.1528(2) -.4010(2) .0379(7) Uani d . 1 . . C H36A .4511 -.1734 -.4472 .046 Uiso calc R 1 . . H H36B .5799 -.1657 -.4295 .046 Uiso calc R 1 . . H C37 .5124(3) -.0453(2) -.3735(2) .0426(8) Uani d . 1 . . C H37A .5762 -.0081 -.3969 .051 Uiso calc R 1 . . H H37B .4475 -.0187 -.4034 .051 Uiso calc R 1 . . H C38 .5050(2) -.1330(2) -.22900(19) .0270(5) Uani d . 1 . . C C39 -.0225(3) -.1984(2) .3430(3) .0440(8) Uani d . 1 . . C H39A -.0553 -.2061 .4047 .066 Uiso calc R 1 . . H H39B -.0676 -.1621 .2984 .066 Uiso calc R 1 . . H H39C .0486 -.1635 .3534 .066 Uiso calc R 1 . . H C40 -.0114(2) -.2987(2) .2994(2) .0334(6) Uani d . 1 . . C C41 .0055(2) -.3066(2) .1976(2) .0322(6) Uani d . 1 . . C C42 .0169(3) -.4028(2) .1493(2) .0391(7) Uani d . 1 . . C H42A -.0444 -.4500 .1609 .047 Uiso calc R 1 . . H H42B .0843 -.4297 .1730 .047 Uiso calc R 1 . . H C43 .0182(3) -.3765(2) .0408(2) .0436(7) Uani d . 1 . . C H43A .0824 -.3989 .0135 .052 Uiso calc R 1 . . H H43B -.0463 -.4072 .0044 .052 Uiso calc R 1 . . H C44 .0098(2) -.2309(2) .1287(2) .0320(6) Uani d . 1 . . C 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 O1 .0274(10) .0429(11) .0313(10) .0031(8) .0021(8) -.0140(9) O2 .0291(10) .0496(12) .0174(9) -.0022(8) .0051(7) -.0094(8) O3 .0497(13) .0371(11) .0295(10) -.0041(9) .0071(9) -.0045(8) O4 .0261(10) .0461(12) .0460(12) -.0011(9) .0054(9) .0263(10) O5 .0263(10) .0233(9) .0446(11) .0008(7) .0010(8) .0146(8) O6 .0473(13) .0397(12) .0367(12) -.0003(10) -.0003(10) .0095(9) N1 .0165(9) .0158(9) .0118(8) .0007(7) .0011(7) .0021(7) N2 .0183(9) .0172(9) .0149(9) .0001(7) .0021(7) .0017(7) C1 .0189(11) .0166(10) .0144(10) -.0011(8) .0027(8) .0042(8) C2 .0213(11) .0193(11) .0194(11) .0005(9) .0021(9) .0071(9) C3 .0240(12) .0215(12) .0206(11) -.0037(9) -.0017(9) .0070(9) C4 .0323(14) .0215(12) .0301(13) -.0032(10) .0010(11) .0103(10) C5 .0187(11) .0181(11) .0148(10) .0023(8) .0011(8) .0038(8) C6 .0226(12) .0199(11) .0210(11) .0027(9) .0049(9) .0061(9) C7 .0260(12) .0220(12) .0241(12) .0057(9) .0042(10) .0102(9) C8 .0358(15) .0254(13) .0317(14) .0077(11) .0096(11) .0148(11) C9 .0177(11) .0200(11) .0143(10) .0008(8) .0035(8) .0028(8) C10 .0212(11) .0276(12) .0149(11) .0008(9) .0024(9) -.0011(9) C11 .0261(13) .0295(13) .0191(11) -.0009(10) .0065(9) -.0032(10) C12 .0384(16) .0397(16) .0228(13) .0009(12) .0094(11) -.0089(11) C13 .0178(11) .0177(11) .0153(10) -.0010(8) -.0009(8) .0002(8) C14 .0237(12) .0248(12) .0166(11) .0021(9) .0012(9) -.0018(9) C15 .0269(13) .0276(13) .0211(12) .0014(10) -.0022(10) -.0028(10) C16 .0420(17) .0469(18) .0257(14) .0007(14) .0008(12) -.0150(12) C17 .0196(11) .0205(11) .0172(11) .0027(9) .0063(8) .0026(9) C18 .0248(12) .0243(12) .0179(11) .0036(9) .0046(9) .0021(9) C19 .0296(13) .0278(13) .0235(12) .0000(10) .0100(10) -.0011(10) C20 .0479(17) .0395(16) .0216(13) .0106(13) .0096(12) -.0014(11) C21 .0190(11) .0202(11) .0179(11) -.0004(9) -.0024(8) .0017(9) C22 .0259(12) .0247(12) .0178(11) .0016(10) .0004(9) -.0001(9) C23 .0336(15) .0379(15) .0235(13) .0040(12) -.0031(11) -.0066(11) C24 .056(2) .055(2) .0250(14) -.0052(16) .0041(13) -.0113(14) C25 .0176(11) .0220(11) .0161(10) .0039(9) .0021(8) .0039(8) C26 .0230(12) .0225(12) .0216(12) .0024(9) .0012(9) .0052(9) C27 .0285(13) .0251(13) .0254(13) .0064(10) .0049(10) .0090(10) C28 .0434(17) .0250(14) .0363(15) .0023(12) .0006(12) .0105(11) C29 .0184(11) .0198(11) .0166(10) -.0029(8) .0023(8) .0027(8) C30 .0219(12) .0199(11) .0178(11) -.0004(9) .0042(9) .0027(9) C31 .0237(12) .0215(12) .0263(12) -.0029(9) -.0010(10) .0048(10) C32 .0341(15) .0221(13) .0386(15) -.0021(11) .0060(12) .0092(11) C33 .0340(15) .0413(16) .0330(15) .0013(12) .0015(12) .0016(12) C34 .0140(11) .0415(15) .0256(13) .0006(10) -.0008(9) -.0060(11) C35 .0218(12) .0398(15) .0193(12) -.0007(10) .0033(9) -.0058(10) C36 .0451(17) .0490(18) .0186(13) -.0035(14) .0040(12) -.0017(12) C37 .0520(19) .0457(18) .0275(15) -.0104(15) .0019(13) .0019(13) C38 .0185(12) .0380(15) .0237(12) -.0030(10) .0027(9) -.0058(11) C39 .0328(16) .0485(19) .0506(19) .0006(14) .0063(14) .0005(15) C40 .0159(12) .0350(15) .0480(17) -.0005(10) -.0028(11) .0043(13) C41 .0259(13) .0300(14) .0399(16) .0007(11) -.0007(11) .0099(12) C42 .0379(16) .0348(16) .0439(17) .0007(12) .0014(13) .0080(13) C43 .0470(19) .0380(17) .0452(18) .0023(14) -.0004(14) .0049(14) C44 .0191(12) .0295(14) .0456(17) -.0002(10) -.0066(11) .0099(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C34 . 1.256(3) y O2 C38 . 1.236(3) y O3 C38 . 1.391(3) y O3 C37 . 1.434(3) y O4 C40 . 1.253(3) y O5 C44 . 1.216(3) y O6 C44 . 1.416(4) n O6 C43 . 1.442(4) n N1 C1 . 1.513(3) n N1 C9 . 1.517(3) n N1 C13 . 1.518(3) n N1 C5 . 1.519(3) n N2 C29 . 1.517(3) n N2 C21 . 1.519(3) n N2 C25 . 1.520(3) n N2 C17 . 1.522(3) n C1 C2 . 1.514(3) n C2 C3 . 1.526(3) n C3 C4 . 1.516(3) n C5 C6 . 1.515(3) n C6 C7 . 1.523(3) n C7 C8 . 1.520(3) n C9 C10 . 1.515(3) n C10 C11 . 1.524(3) n C11 C12 . 1.522(3) n C13 C14 . 1.512(3) n C14 C15 . 1.527(3) n C15 C16 . 1.509(4) n C17 C18 . 1.513(3) n C18 C19 . 1.529(3) n C19 C20 . 1.519(4) n C21 C22 . 1.523(3) n C22 C23 . 1.523(3) n C23 C24 . 1.518(4) n C25 C26 . 1.511(3) n C26 C27 . 1.527(3) n C27 C28 . 1.523(4) n C29 C30 . 1.513(3) n C30 C31 . 1.532(3) n C31 C32 . 1.524(3) n C33 C34 . 1.531(4) n C34 C35 . 1.387(4) y C35 C38 . 1.403(4) y C35 C36 . 1.500(4) n C36 C37 . 1.516(4) n C39 C40 . 1.513(4) n C40 C41 . 1.422(4) y C41 C44 . 1.394(4) y C41 C42 . 1.492(4) n C42 C43 . 1.520(4) n