#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2007311.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_2007311 _journal_name_full 'Acta Crystallographica' _journal_year 1998 _journal_volume C54 _journal_page_first 837 _journal_page_last 840 _publ_section_title ; Lignin Model Compounds: 4,4'-O-Dimethyldehydrodiacetovanillone and 4,4'-O-Diethyldehydrodiacetovanillone ; loop_ _publ_author_name "Ferreira, M\'arcia A." "Costa, M\'arcia D. D." 'Mendes, Isolda M. C.' 'Drumond, Mariza G.' "Pil\'o-Veloso, Dorila" 'Fernandes, Nelson G.' _chemical_formula_sum 'C22 H26 O6' _chemical_formula_weight 386.43 _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 11.4731(4) _cell_length_b 12.2009(4) _cell_length_c 17.6234(7) _cell_angle_alpha 72.477(3) _cell_angle_beta 75.764(3) _cell_angle_gamma 62.294(2) _cell_volume 2066.30(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _exptl_crystal_density_diffrn 1.242 _diffrn_ambient_temperature 298(2) _refine_ls_R_factor_obs .0488 _refine_ls_wR_factor_obs .0562 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_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .0575(2) .3315(2) .64926(13) .0734(7) Uani d . 1 . O O2 .2307(2) .7062(2) .39914(12) .0631(6) Uani d . 1 . O O3 .4431(2) .4984(2) .36774(10) .0509(5) Uani d . 1 . O O4 .8422(2) -.1321(2) .54608(12) .0921(9) Uani d . 1 . O O5 .6221(2) .0709(2) .29155(10) .0618(6) Uani d . 1 . O O6 .4202(2) .2932(2) .31918(11) .0593(6) Uani d . 1 . O O7 -.1910(2) -.0481(2) .06801(12) .0626(6) Uani d . 1 . O O8 .2339(2) -.1859(2) .18393(12) .0639(6) Uani d . 1 . O O9 .2566(2) .0305(2) .16580(11) .0511(5) Uani d . 1 . O O10 .2820(2) .5460(2) -.00897(15) .0863(8) Uani d . 1 . O O11 -.1237(2) .5534(2) .18773(12) .0677(6) Uani d . 1 . O O12 -.1301(2) .3338(2) .20199(13) .0685(6) Uani d D 1 . O C1 .1466(3) .4597(2) .54976(15) .0405(7) Uani d . 1 . C C2 .1359(3) .5798(2) .5071(2) .0458(7) Uani d . 1 . C C3 .2337(3) .5927(2) .4459(2) .0446(7) Uani d . 1 . C C4 .3457(3) .4852(2) .42774(15) .0417(7) Uani d . 1 . C C5 .3570(2) .3641(2) .46834(15) .0385(7) Uani d . 1 . C C6 .2564(3) .3542(2) .5291(2) .0448(7) Uani d . 1 . C C7 .4730(3) .2464(2) .45058(15) .0410(7) Uani d . 1 . C C8 .5028(3) .2150(2) .3768(2) .0457(7) Uani d . 1 . C C9 .6062(3) .0980(2) .3640(2) .0463(7) Uani d . 1 . C C10 .6816(3) .0168(2) .4252(2) .0486(8) Uani d . 1 . C C11 .6536(3) .0466(2) .4995(2) .0438(7) Uani d . 1 . C C12 .5486(3) .1603(2) .51171(15) .0448(7) Uani d . 1 . C C13 .0453(3) .4391(3) .6168(2) .0497(7) Uani d . 1 . C C14 -.0714(3) .5499(3) .6444(2) .0626(9) Uani d . 1 . C C15 .1105(3) .8182(3) .4059(2) .0866(12) Uani d . 1 . C C16 .5190(3) .5541(3) .3836(2) .0655(9) Uani d . 1 . C C17 .5653(4) .6225(4) .3073(2) .123(2) Uani d . 1 . C C18 .7383(3) -.0467(3) .5635(2) .0578(9) Uani d . 1 . C C19 .6912(3) -.0345(3) .6486(2) .0771(11) Uani d . 1 . C C20 .7221(3) -.0469(2) .2774(2) .0707(10) Uani d . 1 . C C21 .4821(3) .3423(3) .2412(2) .0758(11) Uani d . 1 . C C22 .4032(4) .3619(4) .1800(2) .1047(15) Uani d . 1 . C C23 -.0708(3) .0477(2) .09330(15) .0409(7) Uani d . 1 . C C24 .0267(3) -.0696(2) .1247(2) .0460(7) Uani d . 1 . C C25 .1350(3) -.0763(2) .1496(2) .0452(7) Uani d . 1 . C C26 .1497(3) .0346(2) .1405(2) .0424(7) Uani d . 1 . C C27 .0521(3) .1520(2) .11108(15) .0416(7) Uani d . 1 . C C28 -.0588(3) .1570(2) .08852(15) .0437(7) Uani d . 1 . C C29 .0621(3) .2726(2) .1051(2) .0422(7) Uani d . 1 . C C30 -.0290(3) .3583(2) .1505(2) .0471(7) Uani d . 1 . C C31 -.0246(3) .4741(2) .1423(2) .0490(8) Uani d . 1 . C C32 .0738(3) .5013(2) .0904(2) .0511(8) Uani d . 1 . C C33 .1683(3) .4152(3) .0449(2) .0495(8) Uani d . 1 . C C34 .1613(3) .3016(2) .0523(2) .0485(7) Uani d . 1 . C C35 -.1860(3) .0502(3) .0665(2) .0470(7) Uani d . 1 . C C36 -.2969(3) .1757(3) .0382(2) .0697(10) Uani d . 1 . C C37 .2153(3) -.2989(3) .2055(2) .0762(10) Uani d . 1 . C C38 .3829(3) -.0311(3) .1214(2) .0737(10) Uani d . 1 . C C39 .4833(4) -.0113(4) .1420(3) .120(2) Uani d . 1 . C C40 .2746(3) .4502(3) -.0097(2) .0615(9) Uani d . 1 . C C41 .3704(3) .3668(3) -.0653(2) .0877(12) Uani d . 1 . C C42 -.1334(3) .6784(3) .1746(2) .0787(11) Uani d . 1 . C C43 -.1445(15) .3140(10) .2885(3) .131(4) Uani d PD .457(6) 1 C C44 -.0912(13) .1806(9) .3142(8) .141(3) Uani d PD .457(6) 1 C C43A -.0770(8) .2489(11) .2751(3) .131(4) Uani d PD .543(6) 2 C C44A -.1687(11) .2341(11) .3429(5) .141(3) Uani d PD .543(6) 2 C H2A .0627(3) .6516(2) .5198(2) .055 Uiso calc R 1 . H H6A .2629(3) .2739(2) .5568(2) .054 Uiso calc R 1 . H H10A .7522(3) -.0591(2) .4164(2) .058 Uiso calc R 1 . H H12A .5281(3) .1798(2) .56187(15) .054 Uiso calc R 1 . H H14A -.1382(8) .5229(5) .6760(10) .094 Uiso calc R 1 . H H14B -.1070(12) .6148(8) .5987(2) .094 Uiso calc R 1 . H H14C -.0435(5) .5828(12) .6763(10) .094 Uiso calc R 1 . H H15A .1157(10) .8875(6) .3636(9) .130 Uiso calc R 1 . H H15B .0982(13) .8381(13) .4569(7) .130 Uiso calc R 1 . H H15C .0368(4) .8039(8) .4019(14) .130 Uiso calc R 1 . H H16A .5945(3) .4883(3) .4102(2) .079 Uiso calc R 1 . H H16B .4643(3) .6124(3) .4187(2) .079 Uiso calc R 1 . H H17A .621(3) .655(3) .3173(3) .184 Uiso calc R 1 . H H17B .4902(4) .6915(19) .2832(10) .184 Uiso calc R 1 . H H17C .615(3) .5655(9) .2717(8) .184 Uiso calc R 1 . H H19A .7511(13) -.1056(12) .6828(2) .116 Uiso calc R 1 . H H19B .6041(10) -.033(2) .6634(4) .116 Uiso calc R 1 . H H19C .688(2) .0426(11) .6544(3) .116 Uiso calc R 1 . H H20A .7213(14) -.0539(9) .2247(5) .106 Uiso calc R 1 . H H20B .7062(12) -.1142(2) .3167(8) .106 Uiso calc R 1 . H H20C .8070(4) -.0528(8) .2812(12) .106 Uiso calc R 1 . H H21A .4822(3) .4217(3) .2414(2) .091 Uiso calc R 1 . H H21B .5731(3) .2819(3) .2303(2) .091 Uiso calc R 1 . H H22A .4367(18) .400(2) .1287(4) .157 Uiso calc R 1 . H H22B .3122(6) .417(2) .1936(9) .157 Uiso calc R 1 . H H22C .409(2) .2818(5) .1778(12) .157 Uiso calc R 1 . H H24A .0186(3) -.1436(2) .1287(2) .055 Uiso calc R 1 . H H28A -.1259(3) .2354(2) .06993(15) .052 Uiso calc R 1 . H H32A .0776(3) .5777(2) .0855(2) .061 Uiso calc R 1 . H H34A .2235(3) .2444(2) .0216(2) .058 Uiso calc R 1 . H H36A -.3609(11) .1622(3) .0204(12) .105 Uiso calc R 1 . H H36B -.2620(4) .2261(8) -.0054(9) .105 Uiso calc R 1 . H H36C -.3388(14) .2192(9) .0815(4) .105 Uiso calc R 1 . H H37A .2859(12) -.3659(6) .2346(11) .114 Uiso calc R 1 . H H37B .216(2) -.3220(11) .1579(2) .114 Uiso calc R 1 . H H37C .1319(10) -.2855(7) .2387(11) .114 Uiso calc R 1 . H H38A .4068(3) -.1213(3) .1328(2) .088 Uiso calc R 1 . H H38B .3766(3) .0020(3) .0644(2) .088 Uiso calc R 1 . H H39A .5646(9) -.046(3) .1078(12) .180 Uiso calc R 1 . H H39B .497(2) -.053(2) .1969(6) .180 Uiso calc R 1 . H H39C .4561(13) .0780(4) .1353(17) .180 Uiso calc R 1 . H H41A .4356(15) .3984(14) -.0931(11) .132 Uiso calc R 1 . H H41B .3236(5) .3665(19) -.1035(10) .132 Uiso calc R 1 . H H41C .4137(19) .2820(6) -.0350(3) .132 Uiso calc R 1 . H H42A -.2138(11) .7281(7) .2040(11) .118 Uiso calc R 1 . H H42B -.134(2) .7170(8) .1185(3) .118 Uiso calc R 1 . H H42C -.0587(12) .6742(3) .1926(12) .118 Uiso calc R 1 . H H43A -.0952(15) .3483(10) .3043(3) .157 Uiso calc PR .457(6) 1 H H43B -.2370(15) .3529(10) .3103(3) .157 Uiso calc PR .457(6) 1 H H44A -.106(8) .1581(10) .3717(8) .211 Uiso calc PR .457(6) 1 H H44B .0024(19) .1451(11) .297(5) .211 Uiso calc PR .457(6) 1 H H44C -.134(6) .1480(12) .292(4) .211 Uiso calc PR .457(6) 1 H H43C -.0194(8) .1659(11) .2635(3) .157 Uiso calc PR .543(6) 2 H H43D -.0220(8) .2787(11) .2895(3) .157 Uiso calc PR .543(6) 2 H H44D -.172(5) .278(6) .3809(18) .211 Uiso calc PR .543(6) 2 H H44E -.142(4) .1456(12) .367(3) .211 Uiso calc PR .543(6) 2 H H44F -.2552(18) .269(6) .3266(8) .211 Uiso calc PR .543(6) 2 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 O1 .063(2) .0542(14) .079(2) -.0223(12) .0082(12) .0002(12) O2 .0583(14) .0333(11) .0760(14) -.0130(10) .0001(11) .0003(10) O3 .0523(13) .0505(12) .0497(12) -.0242(10) .0034(10) -.0144(9) O4 .069(2) .075(2) .071(2) .0210(14) -.0180(13) -.0100(13) O5 .0680(15) .0481(12) .0504(12) .0000(11) -.0138(11) -.0205(10) O6 .0547(13) .0555(12) .0500(12) -.0039(11) -.0194(11) -.0092(10) O7 .0648(15) .0525(13) .083(2) -.0360(11) -.0176(12) -.0061(11) O8 .0560(14) .0346(11) .093(2) -.0160(10) -.0270(12) .0060(10) O9 .0459(13) .0491(12) .0606(12) -.0189(10) -.0134(10) -.0118(10) O10 .081(2) .059(2) .122(2) -.0461(14) -.0180(15) .0060(14) O11 .081(2) .0368(12) .087(2) -.0270(11) -.0002(13) -.0206(11) O12 .081(2) .0485(13) .075(2) -.0358(12) .0104(13) -.0149(11) C1 .038(2) .035(2) .042(2) -.0119(14) -.0044(13) -.0061(13) C2 .036(2) .038(2) .053(2) -.0044(14) -.0051(15) -.0144(14) C3 .045(2) .032(2) .050(2) -.0115(14) -.0084(15) -.0054(13) C4 .036(2) .044(2) .040(2) -.0150(14) -.0009(13) -.0089(13) C5 .036(2) .033(2) .0399(15) -.0096(13) -.0073(13) -.0062(12) C6 .046(2) .032(2) .050(2) -.0124(14) -.0105(15) -.0031(13) C7 .038(2) .0339(15) .046(2) -.0105(13) -.0035(14) -.0100(13) C8 .040(2) .040(2) .047(2) -.0082(14) -.0104(14) -.0067(14) C9 .047(2) .041(2) .045(2) -.0110(15) -.0043(14) -.0147(13) C10 .043(2) .035(2) .054(2) -.0047(14) -.0042(15) -.0109(14) C11 .040(2) .0352(15) .046(2) -.0081(14) -.0070(14) -.0060(13) C12 .043(2) .044(2) .039(2) -.0127(15) -.0038(14) -.0093(13) C13 .041(2) .050(2) .051(2) -.015(2) -.0056(15) -.008(2) C14 .046(2) .066(2) .062(2) -.016(2) .004(2) -.017(2) C15 .072(3) .037(2) .114(3) -.007(2) .001(2) -.003(2) C16 .059(2) .082(2) .062(2) -.037(2) -.001(2) -.018(2) C17 .157(4) .175(5) .089(3) -.136(4) .016(3) -.016(3) C18 .048(2) .054(2) .053(2) -.010(2) -.010(2) -.004(2) C19 .065(2) .091(3) .054(2) -.013(2) -.021(2) -.008(2) C20 .083(3) .053(2) .054(2) -.007(2) -.002(2) -.023(2) C21 .096(3) .055(2) .051(2) -.004(2) -.027(2) -.007(2) C22 .118(4) .103(3) .072(2) -.010(3) -.038(2) -.029(2) C23 .041(2) .033(2) .048(2) -.0159(14) -.0045(14) -.0083(13) C24 .050(2) .032(2) .056(2) -.0204(15) -.0058(15) -.0064(13) C25 .043(2) .031(2) .054(2) -.0130(14) -.0068(15) -.0020(13) C26 .040(2) .041(2) .047(2) -.0177(14) -.0068(14) -.0087(13) C27 .046(2) .034(2) .045(2) -.0187(14) -.0065(14) -.0064(12) C28 .047(2) .032(2) .050(2) -.0137(14) -.0124(14) -.0061(13) C29 .049(2) .035(2) .046(2) -.0189(14) -.0176(15) -.0004(13) C30 .056(2) .038(2) .050(2) -.022(2) -.012(2) -.0048(14) C31 .060(2) .035(2) .056(2) -.018(2) -.018(2) -.0081(14) C32 .059(2) .035(2) .064(2) -.023(2) -.026(2) .0021(15) C33 .050(2) .043(2) .058(2) -.022(2) -.022(2) .0029(15) C34 .049(2) .041(2) .054(2) -.0166(15) -.015(2) -.0043(14) C35 .045(2) .047(2) .050(2) -.022(2) -.0008(14) -.0118(14) C36 .051(2) .061(2) .102(3) -.019(2) -.025(2) -.021(2) C37 .082(3) .035(2) .102(3) -.022(2) -.032(2) .010(2) C38 .043(2) .071(2) .104(3) -.016(2) -.009(2) -.030(2) C39 .069(3) .170(5) .153(4) -.067(3) .004(3) -.066(4) C40 .056(2) .056(2) .068(2) -.027(2) -.028(2) .015(2) C41 .066(3) .102(3) .089(3) -.043(2) .006(2) -.014(2) C42 .101(3) .045(2) .098(3) -.033(2) -.012(2) -.024(2) C43 .156(10) .182(11) .056(4) -.105(8) .062(5) -.033(5) C44 .141(10) .132(9) .101(7) -.056(7) .034(5) -.002(5) C43A .156(10) .182(11) .056(4) -.105(8) .062(5) -.033(5) C44A .141(10) .132(9) .101(7) -.056(7) .034(5) -.002(5) 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 C13 . 1.220(3) yes O2 C3 . 1.371(3) ? O2 C15 . 1.431(3) yes O3 C4 . 1.369(3) ? O3 C16 . 1.444(3) yes O4 C18 . 1.208(3) yes O5 C9 . 1.363(3) ? O5 C20 . 1.409(3) yes O6 C8 . 1.373(3) ? O6 C21 . 1.473(3) yes O7 C35 . 1.219(3) yes O8 C25 . 1.372(3) ? O8 C37 . 1.417(3) yes O9 C26 . 1.380(3) ? O9 C38 . 1.435(3) yes O10 C40 . 1.215(3) yes O11 C31 . 1.365(3) ? O11 C42 . 1.427(3) yes O12 C30 . 1.378(3) yes O12 C43 . 1.449(5) yes O12 C43A . 1.450(5) yes C1 C6 . 1.388(3) ? C1 C2 . 1.394(3) ? C1 C13 . 1.492(4) yes C2 C3 . 1.383(3) ? C3 C4 . 1.399(3) ? C4 C5 . 1.394(3) ? C5 C6 . 1.392(3) ? C5 C7 . 1.490(3) yes C7 C8 . 1.384(3) ? C7 C12 . 1.396(3) ? C8 C9 . 1.408(3) ? C9 C10 . 1.382(3) ? C10 C11 . 1.387(3) ? C11 C12 . 1.385(3) ? C11 C18 . 1.501(4) yes C13 C14 . 1.500(4) yes C16 C17 . 1.474(4) yes C18 C19 . 1.491(4) yes C21 C22 . 1.471(4) yes C23 C28 . 1.378(3) ? C23 C24 . 1.395(3) ? C23 C35 . 1.495(4) yes C24 C25 . 1.378(4) ? C25 C26 . 1.397(4) ? C26 C27 . 1.386(3) ? C27 C28 . 1.394(4) ? C27 C29 . 1.499(3) yes C29 C30 . 1.378(3) ? C29 C34 . 1.394(4) ? C30 C31 . 1.401(4) ? C31 C32 . 1.371(4) ? C32 C33 . 1.393(4) ? C33 C34 . 1.390(4) ? C33 C40 . 1.502(4) yes C35 C36 . 1.501(4) yes C38 C39 . 1.427(4) yes C40 C41 . 1.495(4) yes C43 C44 . 1.412(6) yes C43A C44A . 1.412(6) yes