data_2010631 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 250 _journal_page_last 251 _publ_section_title ; Absolute configuration of (-)-4-(3,4-dichlorophenyl)-4-(2-pyridyl)butanoic acid: essential information to determine crucial steric features of arpromidine-type histamine H~2~ receptor agonists ; loop_ _publ_author_name 'Manfred Zabel' 'Josef Breu' 'Franz Rau' 'Klaus-J\"urgen Range' 'Volker Krey' 'Anka Uffrecht' 'Armin Buschauer' _chemical_name_common '(R)-(-)-4-(3,4-dichlorophenyl)-4-(2-pyridyl)butanoic acid . L-(-)-ephedrine' _chemical_formula_moiety 'C10 H16 N O+ , C15 H12 Cl2 N O2 -' _chemical_formula_sum 'C25 H28 Cl2 N2 O3' _chemical_formula_weight 475.39 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2y1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.2380(11) _cell_length_b 5.9089(4) _cell_length_c 16.3148(15) _cell_angle_alpha 90.00 _cell_angle_beta 111.335(9) _cell_angle_gamma 90.00 _cell_volume 1188.72(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.328 _diffrn_ambient_temperature 150(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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 -.08340(7) .2067(2) .03262(7) .0470(3) Uani d . 1 . . Cl Cl2 -.17587(7) .66628(19) .07399(7) .0485(3) Uani d . 1 . . Cl O1 .53029(17) .7213(4) .14011(15) .0324(6) Uani d . 1 . . O O2 .4403(2) 1.0127(5) .1677(2) .0431(7) Uani d . 1 . . O C3 .4480(3) .8083(7) .1526(3) .0333(10) Uani d . 1 . . C C4 .3595(3) .6478(7) .1535(2) .0333(10) Uani d . 1 . . C H4A .3628(3) .513(4) .1232(9) .050 Uiso calc R 1 . . H H4B .2907(18) .7151(18) .1248(8) .050 Uiso calc R 1 . . H C5 .3755(3) .5940(6) .2496(2) .0312(10) Uani d . 1 . . C H5A .4437(19) .5436(14) .2770(8) .047 Uiso calc R 1 . . H H5B .3687(3) .723(4) .2762(8) .047 Uiso calc R 1 . . H C6 .2972(3) .4193(7) .2621(2) .0283(9) Uani d . 1 . . C H6 .3096(5) .274(5) .2360(10) .042 Uiso calc R 1 . . H C7 .1778(3) .4853(6) .2142(2) .0285(9) Uani d . 1 . . C C8 .1084(3) .3378(7) .1514(2) .0293(9) Uani d . 1 . . C H8 .1369(12) .193(6) .1373(6) .044 Uiso calc R 1 . . H C9 .0000(3) .3934(7) .1091(2) .0287(9) Uani d . 1 . . C C10 -.0394(3) .5958(7) .1286(3) .0328(10) Uani d . 1 . . C C11 .0270(3) .7413(7) .1885(2) .0366(11) Uani d . 1 . . C H11 .0009(13) .872(6) .2003(6) .055 Uiso calc R 1 . . H C12 .1364(3) .6864(8) .2318(2) .0319(9) Uani d . 1 . . C H12 .179(2) .780(4) .2703(18) .048 Uiso calc R 1 . . H C13 .3262(3) .3801(7) .3601(3) .0293(9) Uani d . 1 . . C N14 .3068(2) .5526(5) .4051(2) .0334(8) Uani d . 1 . . N C15 .3296(3) .5219(8) .4904(3) .0411(11) Uani d . 1 . . C H15 .3115(8) .660(5) .5269(14) .062 Uiso calc R 1 . . H C16 .3745(3) .3290(8) .5362(3) .0408(11) Uani d . 1 . . C H16 .3905(7) .3155(9) .604(3) .061 Uiso calc R 1 . . H C17 .3973(3) .1560(8) .4906(3) .0422(11) Uani d . 1 . . C H17 .4249(17) .043(7) .5152(15) .063 Uiso calc R 1 . . H C18 .3714(2) .1798(8) .3999(2) .0372(10) Uani d . 1 . . C H18 .3837(6) .069(5) .3690(15) .056 Uiso calc R 1 . . H N19 -.3970(2) .2836(5) .15979(19) .0301(8) Uani d . 1 . . N H19A -.4456(12) .170(3) .1727(4) .045 Uiso calc R 1 . . H H19B -.4313(9) .437(4) .1569(2) .045 Uiso calc R 1 . . H C20 -.2893(3) .2840(6) .2360(2) .0288(10) Uani d . 1 . . C H20 -.2481(19) .390(5) .2266(5) .043 Uiso calc R 1 . . H C21 -.2323(3) .0590(7) .2434(3) .0330(9) Uani d . 1 . . C H21 -.2266(4) .0246(14) .184(2) .050 Uiso calc R 1 . . H O22 -.2926(2) -.1181(5) .2630(2) .0482(8) Uani d . 1 . . O H22 -.3495 -.0648 .2669 .072 Uiso calc R 1 . . H C23 -.1183(3) .0595(7) .3124(3) .0316(9) Uani d . 1 . . C C24 -.0817(3) -.1143(8) .3716(3) .0416(11) Uani d . 1 . . C H24 -.130(2) -.232(5) .3717(3) .062 Uiso calc R 1 . . H C25 .0240(3) -.1225(8) .4312(3) .0478(12) Uani d . 1 . . C H25 .0460(12) -.237(6) .4688(19) .072 Uiso calc R 1 . . H C26 .0950(3) .0489(8) .4315(3) .0468(12) Uani d . 1 . . C H26 .169(4) .0444(9) .473(2) .070 Uiso calc R 1 . . H C27 .0604(3) .2257(9) .3735(3) .0459(12) Uani d . 1 . . C H27 .102(2) .325(6) .3738(3) .069 Uiso calc R 1 . . H C28 -.0459(3) .2325(7) .3143(3) .0386(11) Uani d . 1 . . C H28 -.0648(12) .332(6) .2824(19) .058 Uiso calc R 1 . . H C29 -.3936(3) .2322(7) .0725(2) .0419(12) Uani d . 1 . . C H29A -.4598(15) .2359(7) .0328(9) .063 Uiso calc R 1 . . H H29B -.3658(7) .096(3) .0733(2) .063 Uiso calc R 1 . . H H29C -.3532(9) .333(2) .0592(4) .063 Uiso calc R 1 . . H C30 -.3111(3) .3446(7) .3181(2) .0383(11) Uani d . 1 . . C H30A -.3486(8) .493(3) .3097(3) .057 Uiso calc R 1 . . H H30B -.2413(14) .3539(7) .3689(11) .057 Uiso calc R 1 . . H H30C -.3576(10) .227(2) .3297(4) .057 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 Cl1 .0376(5) .0405(7) .0489(6) -.0073(6) -.0012(5) -.0110(6) Cl2 .0297(5) .0428(8) .0657(8) .0000(5) .0085(5) .0021(6) O1 .0294(13) .0248(17) .0407(15) -.0036(13) .0100(12) -.0023(14) O2 .0362(15) .0264(19) .069(2) -.0017(13) .0221(15) -.0025(16) C3 .030(2) .036(3) .029(2) -.0056(18) .0050(18) -.0042(19) C4 .0260(18) .033(3) .036(2) -.0026(17) .0060(17) .0064(19) C5 .0215(18) .033(3) .034(2) -.0055(16) .0042(17) -.0066(18) C6 .026(2) .029(2) .028(2) .0033(17) .0085(18) -.0010(19) C7 .030(2) .024(2) .032(2) -.0042(17) .0127(19) -.0004(18) C8 .031(2) .024(2) .036(2) -.0021(17) .0151(19) .0006(18) C9 .032(2) .022(2) .030(2) -.0047(18) .0092(18) .0045(18) C10 .0244(18) .036(3) .035(2) -.0050(17) .0073(18) .0074(19) C11 .037(2) .032(3) .043(2) .0008(19) .017(2) -.002(2) C12 .0363(19) .025(2) .030(2) -.008(2) .0068(16) -.003(2) C13 .0198(18) .028(3) .038(2) -.0050(17) .0086(18) .000(2) N14 .0329(17) .038(2) .026(2) .0021(15) .0069(15) -.0069(18) C15 .038(2) .042(3) .041(3) .006(2) .011(2) -.001(2) C16 .036(2) .048(3) .036(3) -.008(2) .010(2) .005(2) C17 .034(2) .031(3) .049(3) .000(2) .0007(19) .009(2) C18 .0330(19) .032(3) .042(2) -.001(2) .0080(17) -.006(2) N19 .0298(16) .028(2) .0288(18) -.0034(13) .0059(14) -.0009(14) C20 .029(2) .024(2) .033(2) -.0058(16) .0115(19) -.0004(17) C21 .035(2) .028(3) .033(2) -.0040(19) .0081(19) .0015(19) O22 .0374(15) .0308(18) .068(2) -.0024(14) .0094(16) .0110(16) C23 .029(2) .029(3) .035(2) .0019(18) .0100(18) -.001(2) C24 .034(2) .030(3) .055(3) .000(2) .008(2) .006(2) C25 .037(2) .042(3) .056(3) .003(2) .007(2) .007(2) C26 .028(2) .059(3) .051(3) -.003(2) .011(2) .002(3) C27 .031(2) .058(3) .051(3) -.010(2) .018(2) -.001(3) C28 .040(2) .034(3) .046(3) -.007(2) .020(2) -.002(2) C29 .045(2) .044(3) .036(2) -.010(2) .0139(19) .000(2) C30 .032(2) .052(3) .026(2) .0048(19) .0057(19) .004(2) 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 Cl1 C9 . 1.729(4) yes Cl2 C10 . 1.749(5) yes O1 C3 . 1.286(5) yes O2 C3 . 1.244(5) yes O22 C21 . 1.421(5) yes O22 H22 . .8399 no N14 C15 . 1.325(5) yes N14 C13 . 1.335(5) yes N19 C29 . 1.473(4) yes N19 C20 . 1.513(5) yes N19 H19A . 1.004(17) no N19 H19B . 1.01(2) no C3 C4 . 1.512(6) no C4 C5 . 1.537(4) no C5 C6 . 1.528(6) no C6 C13 . 1.520(6) no C6 C7 . 1.537(6) no C7 C8 . 1.403(5) no C7 C12 . 1.382(6) no C8 C9 . 1.387(6) no C9 C10 . 1.387(6) no C10 C11 . 1.357(6) no C11 C12 . 1.399(6) no C13 C18 . 1.378(6) no C15 C16 . 1.374(7) no C16 C17 . 1.361(7) no C17 C18 . 1.399(5) no C4 H4B . .95(2) no C4 H4A . .95(2) no C5 H5A . .90(2) no C5 H5B . .90(2) no C6 H6 . 1.00(3) no C8 H8 . 1.00(3) no C11 H11 . .90(3) no C12 H12 . .87(3) no C15 H15 . 1.09(3) no C16 H16 . 1.05(5) no C17 H17 . .80(4) no C18 H18 . .88(3) no C20 C21 . 1.512(6) no C20 C30 . 1.512(5) no C21 C23 . 1.519(6) no C23 C28 . 1.394(6) no C23 C24 . 1.372(6) no C24 C25 . 1.384(6) no C25 C26 . 1.381(6) no C26 C27 . 1.372(7) no C27 C28 . 1.388(6) no C20 H20 . .88(3) no C21 H21 . 1.02(3) no C24 H24 . .95(3) no C25 H25 . .89(3) no C26 H26 . .97(5) no C27 H27 . .80(3) no C28 H28 . .76(3) no C29 H29A . .880(18) no C29 H29B . .883(17) no C29 H29C . .879(12) no C30 H30A . .992(17) no C30 H30B . .993(18) no C30 H30C . .991(13) no