data_2011733 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 117 _journal_page_last 119 _publ_section_title ; 4-{[(1E)-(2-Hydroxyphenyl)methylidene]amino}-1,5-dimethyl-2-phenyl-1,2-dihydro -3H-pyrazol-3-one ; loop_ _publ_author_name 'H\"okelek, Tuncer' 'I\,s\?iklan, Muhammed' 'K\?il\?i\,c, Zeynel' _chemical_formula_moiety 'C18 H17 N3 O2' _chemical_formula_sum 'C18 H17 N3 O2' _chemical_formula_weight 307.35 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5950(10) _cell_length_b 7.4980(10) _cell_length_c 27.277(2) _cell_angle_alpha 90 _cell_angle_beta 95.332(7) _cell_angle_gamma 90 _cell_volume 1546.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.320 _diffrn_ambient_temperature 293(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 H1 .793(3) .211(3) -.0155(10) .080(7) Uiso d . 1 . . H N2 .5451(2) .28689(18) .15230(5) .0480(4) Uani d . 1 . . N C1 .8432(2) .3767(3) -.06089(6) .0549(4) Uani d . 1 . . C C2 .9142(3) .4188(3) -.10447(7) .0680(6) Uani d . 1 . . C H21 .9474 .3278 -.1249 .079(7) Uiso calc R 1 . . H C6 .7934(2) .5140(2) -.03010(6) .0471(4) Uani d . 1 . . C C3 .9362(3) .5940(4) -.11783(7) .0701(6) Uani d . 1 . . C H31 .9833 .6203 -.1473 .076(7) Uiso calc R 1 . . H C13 .5347(2) .3386(2) .20201(6) .0468(4) Uani d . 1 . . C C4 .8887(3) .7312(3) -.08782(7) .0659(5) Uani d . 1 . . C H41 .9047 .8495 -.0967 .071(6) Uiso calc R 1 . . H C8 .6428(2) .2796(2) .07716(6) .0442(4) Uani d . 1 . . C C5 .8175(3) .6898(3) -.04459(6) .0570(5) Uani d . 1 . . C H51 .7845 .7818 -.0245 .083(7) Uiso calc R 1 . . H C9 .5966(2) .3992(2) .11537(5) .0440(4) Uani d . 1 . . C C7 .7229(2) .4781(2) .01688(6) .0473(4) Uani d . 1 . . C H71 .6917 .5727 .0363 .048(5) Uiso calc R 1 . . H N3 .5780(2) .10839(18) .14065(5) .0486(4) Uani d . 1 . . N C11 .6569(4) -.0603(3) .06713(8) .0671(6) Uani d . 1 . . C H111 .7257 -.1400 .0888 .120(11) Uiso calc R 1 . . H H112 .7194 -.0353 .0389 .142(13) Uiso calc R 1 . . H H113 .5453 -.1146 .0567 .160(15) Uiso calc R 1 . . H C12 .4574(3) -.0266(2) .15751(7) .0605(5) Uani d . 1 . . C H121 .5008 -.1434 .1507 .093(8) Uiso calc R 1 . . H H122 .3419 -.0110 .1405 .114(10) Uiso calc R 1 . . H H123 .4505 -.0137 .1923 .080(7) Uiso calc R 1 . . H C10 .6266(2) .1089(2) .09357(6) .0481(4) Uani d . 1 . . C C14 .4297(2) .4838(2) .21162(7) .0520(4) Uani d . 1 . . C H141 .3677 .5456 .1860 .065(6) Uiso calc R 1 . . H O1 .8262(2) .20324(19) -.04885(5) .0733(5) Uani d . 1 . . O C15 .4187(3) .5352(3) .26009(7) .0626(5) Uani d . 1 . . C H151 .3490 .6324 .2669 .082(7) Uiso calc R 1 . . H O2 .60176(19) .56281(16) .11860(4) .0579(4) Uani d . 1 . . O C16 .5099(3) .4438(3) .29837(7) .0653(5) Uani d . 1 . . C H161 .5013 .4796 .3307 .074(7) Uiso calc R 1 . . H N1 .70351(19) .31696(18) .03167(5) .0462(3) Uani d . 1 . . N C17 .6137(3) .2996(3) .28866(7) .0613(5) Uani d . 1 . . C H171 .6741 .2374 .3145 .068(6) Uiso calc R 1 . . H C18 .6281(2) .2473(3) .24063(6) .0529(4) Uani d . 1 . . C H181 .6999 .1513 .2341 .065(6) 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 N2 .0676(8) .0362(7) .0418(7) .0019(6) .0137(6) .0009(5) C1 .0630(10) .0592(11) .0428(8) .0003(8) .0067(7) -.0065(7) C2 .0722(12) .0892(15) .0440(9) .0020(11) .0128(8) -.0116(10) C6 .0522(8) .0530(9) .0365(8) .0029(7) .0066(6) .0004(6) C3 .0648(11) .1057(19) .0412(9) -.0053(11) .0120(8) .0100(10) C13 .0542(8) .0457(8) .0426(8) -.0014(7) .0149(6) .0003(6) C4 .0666(11) .0770(14) .0545(10) -.0012(10) .0085(8) .0206(9) C8 .0541(8) .0398(8) .0396(7) .0003(6) .0089(6) -.0003(6) C5 .0662(10) .0577(11) .0482(9) .0042(8) .0105(8) .0074(8) C9 .0560(8) .0371(8) .0402(7) .0004(6) .0107(6) .0012(5) C7 .0584(9) .0444(8) .0399(8) .0033(7) .0095(6) -.0005(6) N3 .0674(8) .0340(7) .0459(7) -.0011(6) .0136(6) .0013(5) C11 .1047(16) .0409(9) .0582(11) -.0003(10) .0201(11) -.0045(8) C12 .0730(12) .0446(10) .0662(12) -.0077(8) .0193(9) .0056(8) C10 .0604(9) .0401(9) .0448(8) -.0007(7) .0097(7) -.0005(6) C14 .0583(9) .0482(9) .0513(9) .0038(7) .0140(7) .0011(7) O1 .1062(12) .0572(9) .0596(8) .0011(7) .0242(8) -.0135(6) C15 .0717(11) .0579(11) .0619(11) .0011(9) .0256(9) -.0072(8) O2 .0862(9) .0362(6) .0542(7) -.0002(5) .0217(6) -.0003(5) C16 .0820(13) .0726(13) .0444(9) -.0043(10) .0219(8) -.0056(8) N1 .0567(7) .0436(7) .0391(7) -.0011(6) .0079(5) -.0014(5) C17 .0701(11) .0710(12) .0440(9) -.0010(9) .0122(8) .0057(8) C18 .0599(9) .0531(10) .0475(9) .0060(8) .0139(7) .0030(7) 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 N2 C9 . 1.3963(19) yes N2 N3 . 1.4034(18) yes N2 C13 . 1.4194(19) yes C1 O1 . 1.351(2) yes C1 C2 . 1.387(3) ? C1 C6 . 1.403(2) n C2 C3 . 1.378(4) ? C2 H21 . .9300 ? C6 C5 . 1.392(2) ? C6 C7 . 1.459(2) yes C3 C4 . 1.383(3) ? C3 H31 . .9300 ? C13 C14 . 1.389(2) ? C13 C18 . 1.393(2) ? C4 C5 . 1.378(2) ? C4 H41 . .9300 ? C8 C10 . 1.366(2) yes C8 N1 . 1.3916(19) yes C8 C9 . 1.443(2) yes C5 H51 . .9300 ? C9 O2 . 1.230(2) yes C7 N1 . 1.287(2) yes C7 H71 . .9300 ? N3 C10 . 1.369(2) yes N3 C12 . 1.468(2) ? C11 C10 . 1.487(2) ? C11 H111 . .9600 ? C11 H112 . .9600 ? C11 H113 . .9600 ? C12 H121 . .9600 ? C12 H122 . .9600 ? C12 H123 . .9600 ? C14 C15 . 1.387(3) ? C14 H141 . .9300 ? O1 H1 . .97(3) yes C15 C16 . 1.380(3) ? C15 H151 . .9300 ? C16 C17 . 1.378(3) ? C16 H161 . .9300 ? C17 C18 . 1.382(2) ? C17 H171 . .9300 ? C18 H181 . .9300 ?