data_2011420 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 1222 _journal_page_last 1224 _publ_section_title ; Hydrogen bonding and C-H...O interactions in 2-[1-(1-naphthyl)ethyl]benzoic acid at 150 K ; loop_ _publ_author_name 'Gerkin, Roger E.' _chemical_name_common ; 2-[1-(1-naphthyl)ethyl]benzoic acid ; _chemical_formula_moiety 'C19 H16 O2' _chemical_formula_sum 'C19 H16 O2' _chemical_formula_weight 276.33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n n a' _symmetry_space_group_name_Hall '-P 2a 2bc' loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y, +z' ' +x,1/2-y,1/2-z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x, +y, -z' ' -x,1/2+y,1/2+z' '1/2+x,1/2-y,1/2+z' _cell_length_a 16.8468(3) _cell_length_b 37.3753(7) _cell_length_c 13.8418(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 8715.5(7) _cell_formula_units_Z 24 _cell_measurement_temperature 150 _exptl_crystal_density_diffrn 1.263 _diffrn_ambient_temperature 150 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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy O1 .65905(5) .24136(3) .34322(6) .0656(4) Uani d ? . 1.000 O2 .52933(5) .23514(2) .33470(6) .0473(3) Uani d ? . 1.000 O3 .33206(5) .55083(3) .66746(7) .0488(3) Uani d ? . 1.000 O4 .25596(5) .59842(2) .64541(6) .0476(3) Uani d ? . 1.000 O5 .25809(5) .62162(3) .82598(7) .0516(3) Uani d ? . 1.000 O6 .33439(5) .57388(2) .84716(6) .0432(3) Uani d ? . 1.000 C1 .59125(7) .22586(3) .48705(9) .0299(4) Uani d ? . 1.000 C2 .52432(7) .23115(3) .54617(9) .0281(4) Uani d ? . 1.000 C3 .53084(7) .22138(3) .64277(9) .0335(4) Uani d ? . 1.000 C4 .60003(8) .20769(3) .68136(9) .0392(4) Uani d ? . 1.000 C5 .66591(7) .20362(3) .62286(10) .0395(4) Uani d ? . 1.000 C6 .66149(7) .21231(3) .52663(10) .0374(4) Uani d ? . 1.000 C7 .59279(7) .23481(3) .38279(9) .0350(4) Uani d ? . 1.000 C8 .44564(7) .24731(3) .51219(9) .0300(4) Uani d ? . 1.000 C9 .38460(9) .21722(4) .50015(13) .0428(5) Uani d ? . 1.000 C10 .42012(7) .27734(3) .57976(8) .0295(4) Uani d ? . 1.000 C11 .35453(7) .27506(4) .63766(9) .0395(4) Uani d ? . 1.000 C12 .33351(8) .30299(4) .70202(10) .0464(5) Uani d ? . 1.000 C13 .37998(8) .33250(4) .70909(9) .0453(5) Uani d ? . 1.000 C14 .49580(9) .36757(4) .65575(9) .0442(5) Uani d ? . 1.000 C15 .55948(8) .37188(4) .59706(10) .0468(5) Uani d ? . 1.000 C16 .57680(7) .34607(4) .52707(10) .0393(4) Uani d ? . 1.000 C17 .53210(7) .31568(3) .52058(9) .0314(4) Uani d ? . 1.000 C18 .46699(7) .30942(3) .58281(8) .0286(4) Uani d ? . 1.000 C19 .44736(7) .33681(4) .65026(9) .0347(4) Uani d ? . 1.000 C20 .28444(7) .56082(3) .50974(8) .0268(4) Uani d ? . 1.000 C21 .21975(7) .56903(3) .44954(8) .0255(4) Uani d ? . 1.000 C22 .22503(7) .55861(3) .35359(8) .0318(4) Uani d ? . 1.000 C23 .29113(8) .54131(3) .31688(9) .0354(4) Uani d ? . 1.000 C24 .35416(7) .53310(3) .37661(9) .0350(4) Uani d ? . 1.000 C25 .35000(7) .54248(3) .47273(9) .0331(4) Uani d ? . 1.000 C26 .28821(7) .57168(4) .61280(9) .0303(4) Uani d ? . 1.000 C27 .14141(7) .58482(3) .48680(9) .0274(4) Uani d ? . 1.000 C28 .08931(9) .55373(4) .52112(11) .0363(5) Uani d ? . 1.000 C29 .10165(7) .60894(3) .41214(8) .0267(4) Uani d ? . 1.000 C30 .03386(7) .59899(3) .36444(9) .0331(4) Uani d ? . 1.000 C31 -.00181(7) .62103(4) .29413(9) .0373(4) Uani d ? . 1.000 C32 .03000(7) .65338(4) .27208(9) .0343(4) Uani d ? . 1.000 C33 .13415(8) .69900(3) .29728(8) .0344(4) Uani d ? . 1.000 C34 .20022(7) .71051(3) .34405(9) .0381(4) Uani d ? . 1.000 C35 .23537(7) .68930(4) .41579(9) .0368(4) Uani d ? . 1.000 C36 .20426(7) .65654(3) .43850(8) .0309(4) Uani d ? . 1.000 C37 .13577(7) .64329(3) .39103(8) .0251(4) Uani d ? . 1.000 C38 .09964(7) .66538(3) .31962(8) .0280(4) Uani d ? . 1.000 C39 .29434(7) .60750(3) .98608(8) .0272(4) Uani d ? . 1.000 C40 .35789(7) .60071(3) 1.04936(8) .0247(4) Uani d ? . 1.000 C41 .34601(7) .60770(3) 1.14677(8) .0293(4) Uani d ? . 1.000 C42 .27428(7) .62036(3) 1.18174(8) .0324(4) Uani d ? . 1.000 C43 .21242(7) .62715(3) 1.11899(9) .0348(4) Uani d ? . 1.000 C44 .22309(7) .62116(3) 1.02166(9) .0346(4) Uani d ? . 1.000 C45 .29849(7) .59938(4) .88138(9) .0314(4) Uani d ? . 1.000 C46 .44084(7) .59059(3) 1.01340(9) .0270(4) Uani d ? . 1.000 C47 .48486(8) .62547(4) .99057(11) .0386(5) Uani d ? . 1.000 C48 .48455(6) .56602(3) 1.08276(8) .0266(4) Uani d ? . 1.000 C49 .55173(7) .57673(3) 1.13069(8) .0332(4) Uani d ? . 1.000 C50 .59298(7) .55381(4) 1.19378(9) .0432(5) Uani d ? . 1.000 C51 .56687(8) .52018(4) 1.20933(9) .0453(5) Uani d ? . 1.000 C52 .47076(9) .47205(4) 1.17614(10) .0500(5) Uani d ? . 1.000 C53 .40560(10) .45970(4) 1.12999(11) .0537(5) Uani d ? . 1.000 C54 .36380(8) .48187(4) 1.06503(10) .0475(5) Uani d ? . 1.000 C55 .38868(7) .51633(3) 1.04893(9) .0362(4) Uani d ? . 1.000 C56 .45634(7) .53024(3) 1.09708(8) .0286(4) Uani d ? . 1.000 C57 .49851(7) .50734(4) 1.16161(9) .0354(4) Uani d ? . 1.000 H1O3 .3311(9) .5608(4) .7339(12) .111(6) Uiso d ? . 1.000 H1O5 .2603(10) .6120(5) .7532(13) .132(7) Uiso d ? . 1.000 H1O1 .6572 .2493 .2570 .156 Uiso d ? . .500 H1O2 .5288 .2489 .2565 .113 Uiso d ? . .500 H3 .4846 .2243 .6850 .040 Uiso c C3 . 1.000 H4 .6024 .2009 .7497 .047 Uiso c C4 . 1.000 H5 .7157 .1945 .6500 .047 Uiso c C5 . 1.000 H6 .7081 .2090 .4852 .045 Uiso c C6 . 1.000 H8 .4523(5) .2582(3) .4476(7) .022(3) Uiso d ? . 1.000 H9B .3308(7) .2264(3) .4746(8) .044(4) Uiso d ? . 1.000 H9C .4046(7) .1990(3) .4521(9) .054(4) Uiso d ? . 1.000 H9A .3739(7) .2041(3) .5624(9) .047(4) Uiso d ? . 1.000 H11 .3212 .2536 .6346 .047 Uiso c C11 . 1.000 H12 .2854 .3010 .7414 .056 Uiso c C12 . 1.000 H13 .3664 .3511 .7560 .054 Uiso c C13 . 1.000 H14 .4831 .3862 .7031 .053 Uiso c C14 . 1.000 H15 .5933 .3931 .6037 .056 Uiso c C15 . 1.000 H16 .6212 .3498 .4825 .047 Uiso c C16 . 1.000 H17 .5455 .2978 .4716 .038 Uiso c C17 . 1.000 H22 .1804 .5637 .3103 .038 Uiso c C22 . 1.000 H23 .2932 .5349 .2483 .042 Uiso c C23 . 1.000 H24 .4011 .5208 .3511 .042 Uiso c C24 . 1.000 H25 .3939 .5362 .5160 .040 Uiso c C25 . 1.000 H27 .1534(5) .6001(3) .5430(7) .020(3) Uiso d ? . 1.000 H28B .1180(6) .5401(3) .5746(8) .042(4) Uiso d ? . 1.000 H28C .0767(6) .5364(3) .4660(8) .039(4) Uiso d ? . 1.000 H28A .0368(7) .5625(3) .5493(8) .045(4) Uiso d ? . 1.000 H30 .0095 .5759 .3797 .040 Uiso c C30 . 1.000 H31 -.0500 .6129 .2609 .045 Uiso c C31 . 1.000 H32 .0047 .6685 .2231 .041 Uiso c C32 . 1.000 H33 .1100 .7141 .2474 .041 Uiso c C33 . 1.000 H34 .2234 .7338 .3276 .046 Uiso c C34 . 1.000 H35 .2826 .6980 .4499 .044 Uiso c C35 . 1.000 H36 .2298 .6420 .4885 .037 Uiso c C36 . 1.000 H41 .3897 .6036 1.1922 .035 Uiso c C41 . 1.000 H42 .2675 .6245 1.2511 .039 Uiso c C42 . 1.000 H43 .1615 .6361 1.1434 .042 Uiso c C43 . 1.000 H44 .1799 .6266 .9766 .041 Uiso c C44 . 1.000 H46 .4348(5) .5770(3) .9531(7) .019(3) Uiso d ? . 1.000 H47C .4906(6) .6422(3) 1.0521(9) .054(4) Uiso d ? . 1.000 H47A .4529(6) .6396(3) .9415(8) .046(4) Uiso d ? . 1.000 H47B .5395(7) .6206(3) .9632(8) .046(4) Uiso d ? . 1.000 H49 .5716 .6011 1.1207 .040 Uiso c C49 . 1.000 H50 .6410 .5623 1.2266 .052 Uiso c C50 . 1.000 H51 .5956 .5045 1.2542 .054 Uiso c C51 . 1.000 H52 .4994 .4562 1.2206 .060 Uiso c C52 . 1.000 H53 .3873 .4352 1.1417 .064 Uiso c C53 . 1.000 H54 .3169 .4726 1.0313 .057 Uiso c C54 . 1.000 H55 .3593 .5315 1.0036 .043 Uiso c C55 . 1.000 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 .0304(5) .1149(10) .0516(6) -.0132(6) .0037(5) .0107(6) O2 .0304(5) .0773(8) .0342(5) -.0056(5) -.0033(5) -.0091(5) O3 .0653(7) .0505(7) .0306(6) .0291(5) -.0124(5) -.0046(5) O4 .0609(6) .0510(7) .0310(5) .0281(5) -.0119(5) -.0124(5) O5 .0632(6) .0601(7) .0316(6) .0319(5) -.0132(5) -.0055(5) O6 .0496(6) .0503(7) .0297(5) .0209(5) -.0081(4) -.0098(5) C1 .0244(7) .0269(8) .0384(8) -.0025(6) -.0021(6) -.0042(6) C2 .0259(7) .0223(8) .0361(8) -.0015(6) -.0044(6) -.0048(6) C3 .0318(7) .0306(8) .0382(8) .0006(6) -.0006(7) -.0018(7) C4 .0413(8) .0335(9) .0428(8) .0027(7) -.0087(7) .0040(7) C5 .0318(8) .0290(9) .0578(10) .0033(6) -.0113(8) .0016(7) C6 .0262(7) .0335(9) .0526(10) .0013(6) -.0008(7) -.0041(7) C7 .0246(8) .0374(9) .0431(9) .0002(7) .0010(7) -.0097(7) C8 .0254(7) .0344(9) .0301(8) -.0019(6) -.0019(6) .0004(7) C9 .0302(8) .0476(11) .0507(11) -.0084(8) -.0045(8) -.0013(9) C10 .0232(7) .0380(9) .0273(7) .0065(6) -.0031(6) .0050(7) C11 .0298(7) .0485(10) .0402(8) .0051(7) .0026(7) .0075(7) C12 .0359(8) .0646(12) .0387(9) .0193(8) .0122(7) .0050(8) C13 .0501(9) .0501(11) .0356(8) .0217(8) .0009(7) -.0022(8) C14 .0632(10) .0308(9) .0385(9) .0135(8) -.0104(8) -.0064(7) C15 .0563(10) .0315(9) .0526(10) -.0003(8) -.0132(8) .0017(8) C16 .0373(8) .0329(9) .0477(9) .0026(7) -.0040(7) .0061(7) C17 .0302(7) .0285(8) .0355(8) .0052(6) -.0029(6) .0013(6) C18 .0274(7) .0308(8) .0276(7) .0089(6) -.0055(6) .0018(6) C19 .0386(8) .0371(9) .0284(8) .0128(7) -.0045(7) .0005(7) C20 .0331(7) .0223(8) .0251(7) .0020(6) .0018(6) -.0001(6) C21 .0326(7) .0192(7) .0246(7) -.0011(6) .0023(6) .0021(6) C22 .0404(8) .0285(8) .0263(7) .0029(6) -.0006(6) .0013(6) C23 .0525(9) .0268(8) .0268(8) -.0001(7) .0087(7) -.0020(6) C24 .0396(8) .0292(8) .0362(8) .0064(7) .0096(7) -.0002(7) C25 .0353(8) .0293(8) .0348(8) .0043(7) .0014(6) .0007(6) C26 .0300(7) .0297(9) .0311(8) .0048(7) -.0025(6) .0002(7) C27 .0328(7) .0266(8) .0226(7) .0019(7) -.0008(6) -.0010(6) C28 .0390(9) .0360(10) .0339(9) .0014(8) .0042(8) .0045(8) C29 .0291(7) .0294(8) .0217(7) .0050(6) .0010(6) -.0029(6) C30 .0371(8) .0301(8) .0321(8) -.0017(7) -.0018(6) -.0021(6) C31 .0351(8) .0427(10) .0341(8) .0017(7) -.0109(6) -.0029(7) C32 .0383(8) .0373(9) .0272(8) .0100(7) -.0047(6) .0000(7) C33 .0412(8) .0329(9) .0290(8) .0077(7) .0028(7) .0046(6) C34 .0439(8) .0291(9) .0412(9) -.0001(7) .0041(7) .0042(7) C35 .0337(8) .0346(9) .0421(9) .0002(7) -.0031(7) -.0011(7) C36 .0319(7) .0301(9) .0306(8) .0055(7) -.0013(6) -.0008(7) C37 .0253(7) .0273(8) .0227(7) .0050(6) .0019(6) -.0033(6) C38 .0314(7) .0313(8) .0212(7) .0080(7) .0028(6) -.0030(6) C39 .0274(7) .0294(8) .0248(7) .0003(6) .0015(6) -.0016(6) C40 .0278(7) .0217(7) .0247(7) -.0002(6) .0026(6) .0008(6) C41 .0326(7) .0291(8) .0262(7) .0013(6) -.0003(6) .0013(6) C42 .0417(8) .0300(8) .0256(7) -.0026(7) .0082(7) .0002(6) C43 .0291(7) .0363(9) .0390(8) .0005(6) .0082(7) -.0058(7) C44 .0258(7) .0415(9) .0364(8) .0015(6) -.0024(6) -.0042(7) C45 .0247(7) .0388(9) .0306(8) .0050(7) -.0037(6) -.0013(7) C46 .0284(7) .0297(8) .0229(7) .0019(6) -.0012(6) -.0002(7) C47 .0316(9) .0417(10) .0423(10) .0031(8) .0061(8) .0124(8) C48 .0273(7) .0309(8) .0216(7) .0056(6) .0028(6) -.0008(6) C49 .0342(7) .0359(9) .0296(7) .0042(7) -.0027(6) -.0016(7) C50 .0403(8) .0517(11) .0376(9) .0107(8) -.0115(7) -.0047(8) C51 .0570(10) .0496(11) .0294(8) .0242(8) -.0069(7) .0014(8) C52 .0772(11) .0368(10) .0361(9) .0143(9) .0185(8) .0045(8) C53 .0800(12) .0283(10) .0528(10) -.0022(9) .0306(9) .0002(8) C54 .0487(9) .0395(10) .0545(10) -.0065(8) .0163(8) -.0110(8) C55 .0370(8) .0323(9) .0392(8) .0003(7) .0087(7) -.0056(7) C56 .0347(8) .0275(8) .0236(7) .0054(7) .0077(6) -.0022(6) C57 .0498(9) .0294(9) .0270(8) .0113(7) .0104(7) .0013(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 . . 1.2672(13) yes O1 H1O1 . . 1.23 no O2 C7 . . 1.2596(13) yes O2 H1O2 . . 1.20 no O3 C26 . . 1.3135(13) yes O3 H1O3 . . .994(17) no O4 C26 . . 1.2239(13) yes O5 C45 . . 1.3200(13) yes O5 H1O5 . . 1.070(18) no O6 C45 . . 1.2240(13) yes C1 C2 . . 1.4073(15) no C1 C6 . . 1.3988(15) no C1 C7 . . 1.4817(16) no C2 C3 . . 1.3905(16) no C2 C8 . . 1.5305(15) no C3 C4 . . 1.3804(15) no C3 H3 . . .98 no C4 C5 . . 1.3823(16) no C4 H4 . . .98 no C5 C6 . . 1.3731(17) no C5 H5 . . .98 no C6 H6 . . .98 no C8 C9 . . 1.5329(17) no C8 C10 . . 1.5231(16) nos C8 H8 . . .988(9) no C9 H9B . . 1.033(12) no C9 H9C . . 1.010(12) no C9 H9A . . 1.009(11) no C10 C11 . . 1.3676(15) no C10 C18 . . 1.4364(15) no C11 C12 . . 1.4172(17) no C11 H11 . . .98 no C12 C13 . . 1.3561(17) no C12 H12 . . .98 no C13 C19 . . 1.4062(16) no C13 H13 . . .98 no C14 C15 . . 1.3554(17) no C14 C19 . . 1.4119(17) no C14 H14 . . .98 no C15 C16 . . 1.3980(17) no C15 H15 . . .98 no C16 C17 . . 1.3656(16) no C16 H16 . . .98 no C17 C18 . . 1.4141(15) no C17 H17 . . .98 no C18 C19 . . 1.4244(16) no C20 C21 . . 1.4057(15) no C20 C25 . . 1.3971(15) no C20 C26 . . 1.4845(15) no C21 C22 . . 1.3868(15) no C21 C27 . . 1.5349(15) no C22 C23 . . 1.3845(15) no C22 H22 . . .98 no C23 C24 . . 1.3802(16) no C23 H23 . . .98 no C24 C25 . . 1.3777(15) no C24 H24 . . .98 no C25 H25 . . .98 no C27 C28 . . 1.5319(17) no C27 C29 . . 1.5261(15) no C27 H27 . . .985(9) no C28 H28B . . 1.020(11) no C28 H28C . . 1.024(11) no C28 H28A . . 1.021(11) no C29 C30 . . 1.3706(15) no C29 C37 . . 1.4367(15) no C30 C31 . . 1.4095(16) no C30 H30 . . .98 no C31 C32 . . 1.3573(16) no C31 H31 . . .98 no C32 C38 . . 1.4179(15) no C32 H32 . . .98 no C33 C34 . . 1.3577(16) no C33 C38 . . 1.4186(16) no C33 H33 . . .98 no C34 C35 . . 1.4020(16) no C34 H34 . . .98 no C35 C36 . . 1.3685(15) no C35 H35 . . .98 no C36 C37 . . 1.4172(15) no C36 H36 . . .98 no C37 C38 . . 1.4244(15) no C39 C40 . . 1.4064(15) no C39 C44 . . 1.3942(15) no C39 C45 . . 1.4823(16) no C40 C41 . . 1.3879(14) no C40 C46 . . 1.5309(15) no C41 C42 . . 1.3851(15) no C41 H41 . . .98 no C42 C43 . . 1.3802(16) no C42 H42 . . .98 no C43 C44 . . 1.3775(16) no C43 H43 . . .98 no C44 H44 . . .98 no C46 C47 . . 1.5330(17) no C46 C48 . . 1.5190(15) no C46 H46 . . .982(9) no C47 H47C . . 1.062(12) no C47 H47A . . 1.016(12) no C47 H47B . . 1.011(11) no C48 C49 . . 1.3717(15) no C48 C56 . . 1.4328(15) no C49 C50 . . 1.4070(16) no C49 H49 . . .98 no C50 C51 . . 1.3488(17) no C50 H50 . . .98 no C51 C57 . . 1.4117(17) no C51 H51 . . .98 no C52 C53 . . 1.3512(18) no C52 C57 . . 1.4139(18) no C52 H52 . . .98 no C53 C54 . . 1.4111(18) no C53 H53 . . .98 no C54 C55 . . 1.3724(16) no C54 H54 . . .98 no C55 C56 . . 1.4191(15) no C55 H55 . . .98 no C56 C57 . . 1.4267(16) no