#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2008265.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_2008265 _journal_name_full 'Acta Crystallographica' _journal_year 1999 _journal_volume C55 _journal_page_first 407 _journal_page_last 410 _publ_section_title ; 6-[N-(2-Hydroxyphenyl)aminomethylene]cyclohexa-2,4-dien-1-one ; loop_ _publ_author_name 'Alok K. Mukherjee' 'Rajib Lal De' 'Indrajit Banerjee' 'Chitra Samanta' 'Nirmalya P. Nayak' _chemical_name_common ; '6-[N-(2-Hydroxyphenyl)aminomethylene]cyclohexa-2,4-dien-1-one' ; _chemical_formula_moiety 'C13 H11 N1 O2' _chemical_formula_sum 'C13 H11 N1 O2' _chemical_formula_structural 'C13 H11 N1 O2' _chemical_formula_analytical 'C13 H11 N1 O2' _chemical_formula_weight 213.23 _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 9.034(2) _cell_length_b 10.1550(10) _cell_length_c 12.368(2) _cell_angle_alpha 110.350(10) _cell_angle_beta 89.90(2) _cell_angle_gamma 103.020(10) _cell_volume 1032.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.371 _diffrn_ambient_temperature 293(2) _refine_ls_R_factor_obs 0.0499 _refine_ls_wR_factor_obs 0.1248 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 0.58716(14) 0.09552(13) 0.72417(10) 0.0543(3) Uani d . 1 . O O2 0.83069(13) -0.14304(12) 0.60901(9) 0.0496(3) Uani d . 1 . O O3 0.96496(14) 0.10397(13) 1.23118(10) 0.0559(3) Uani d . 1 . O O4 0.60168(13) -0.13305(12) 1.11688(9) 0.0499(3) Uani d . 1 . O N1 0.72941(13) 0.02935(13) 0.53071(10) 0.0367(3) Uani d . 1 . N N2 0.79135(13) 0.03729(13) 1.03742(10) 0.0374(3) Uani d . 1 . N C1 0.5857(2) 0.1789(2) 0.66010(12) 0.0384(3) Uani d . 1 . C C2 0.5154(2) 0.2939(2) 0.69069(13) 0.0451(3) Uani d . 1 . C C3 0.5154(2) 0.3718(2) 0.6197(2) 0.0548(4) Uani d . 1 . C C4 0.5840(3) 0.3369(2) 0.5165(2) 0.0653(5) Uani d . 1 . C C5 0.6553(2) 0.2237(2) 0.48518(14) 0.0521(4) Uani d . 1 . C C6 0.6569(2) 0.14492(15) 0.55635(12) 0.0359(3) Uani d . 1 . C C7 0.7863(2) -0.03097(15) 0.43462(12) 0.0375(3) Uani d . 1 . C C8 0.8584(2) -0.14605(15) 0.41726(12) 0.0363(3) Uani d . 1 . C C9 0.9132(2) -0.2059(2) 0.30808(12) 0.0426(3) Uani d . 1 . C C10 0.9825(2) -0.3183(2) 0.28669(14) 0.0486(4) Uani d . 1 . C C11 0.9954(2) -0.3753(2) 0.3727(2) 0.0546(4) Uani d . 1 . C C12 0.9437(2) -0.3197(2) 0.4795(2) 0.0545(4) Uani d . 1 . C C13 0.8746(2) -0.2013(2) 0.50734(12) 0.0405(3) Uani d . 1 . C C14 1.0112(2) 0.1862(2) 1.16588(12) 0.0390(3) Uani d . 1 . C C15 1.1404(2) 0.2993(2) 1.19593(13) 0.0443(3) Uani d . 1 . C C16 1.1830(2) 0.3758(2) 1.12338(15) 0.0516(4) Uani d . 1 . C C17 1.0967(2) 0.3406(2) 1.0203(2) 0.0595(5) Uani d . 1 . C C18 0.9669(2) 0.2289(2) 0.99000(14) 0.0506(4) Uani d . 1 . C C19 0.9231(2) 0.1520(2) 1.06287(12) 0.0372(3) Uani d . 1 . C C20 0.7054(2) -0.02493(15) 0.94074(12) 0.0384(3) Uani d . 1 . C C21 0.5754(2) -0.1394(2) 0.92322(12) 0.0379(3) Uani d . 1 . C C22 0.4908(2) -0.2016(2) 0.81447(13) 0.0437(3) Uani d . 1 . C C23 0.3664(2) -0.3144(2) 0.79246(14) 0.0498(4) Uani d . 1 . C C24 0.3240(2) -0.3696(2) 0.8797(2) 0.0587(5) Uani d . 1 . C C25 0.4016(2) -0.3117(2) 0.9873(2) 0.0575(4) Uani d . 1 . C C26 0.5296(2) -0.1929(2) 1.01461(13) 0.0409(3) Uani d . 1 . C H1O 0.5419 0.1244 0.7820 0.129(11) Uiso d . 1 . H H3O 1.0249 0.1326 1.2893 0.070(6) Uiso d . 1 . H H1N 0.7454 -0.0074 0.5805 0.066(6) Uiso d . 1 . H H2N 0.7612 -0.0035 1.0873 0.090(8) Uiso d . 1 . H H2C 0.4674 0.3194 0.7630 0.057(5) Uiso d . 1 . H H3C 0.4705 0.4551 0.6424 0.076(7) Uiso d . 1 . H H4C 0.5835 0.3917 0.4677 0.087(7) Uiso d . 1 . H H5C 0.7019 0.1999 0.4161 0.069(6) Uiso d . 1 . H H7C 0.7749 -0.0004 0.3727 0.053(5) Uiso d . 1 . H H9C 0.9023 -0.1597 0.2534 0.058(5) Uiso d . 1 . H H10C 1.0197 -0.3567 0.2154 0.074(6) Uiso d . 1 . H H11C 1.0345 -0.4601 0.3544 0.067(6) Uiso d . 1 . H H12C 0.9534 -0.3606 0.5349 0.100(8) Uiso d . 1 . H H15C 1.1990 0.3228 1.2653 0.057(5) Uiso d . 1 . H H16C 1.2707 0.4569 1.1470 0.070(6) Uiso d . 1 . H H17C 1.1264 0.3909 0.9712 0.080(7) Uiso d . 1 . H H18C 0.9084 0.2060 0.9213 0.068(6) Uiso d . 1 . H H20C 0.7274 0.0071 0.8788 0.064(6) Uiso d . 1 . H H22C 0.5207 -0.1651 0.7564 0.062(5) Uiso d . 1 . H H23C 0.3103 -0.3543 0.7209 0.055(5) Uiso d . 1 . H H24C 0.2411 -0.4489 0.8646 0.077(7) Uiso d . 1 . H H25C 0.3697 -0.3512 1.0431 0.101(8) Uiso d . 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 O1 0.0720(8) 0.0596(7) 0.0482(6) 0.0301(6) 0.0261(6) 0.0313(5) O2 0.0596(7) 0.0626(7) 0.0389(5) 0.0269(5) 0.0086(5) 0.0256(5) O3 0.0625(7) 0.0654(7) 0.0470(6) 0.0063(6) -0.0044(5) 0.0341(6) O4 0.0545(7) 0.0605(7) 0.0392(5) 0.0123(5) 0.0116(5) 0.0244(5) N1 0.0355(6) 0.0444(6) 0.0354(6) 0.0139(5) 0.0043(4) 0.0179(5) N2 0.0367(6) 0.0451(6) 0.0367(6) 0.0150(5) 0.0097(5) 0.0191(5) C1 0.0367(7) 0.0427(7) 0.0376(7) 0.0093(5) 0.0057(5) 0.0167(6) C2 0.0441(8) 0.0491(8) 0.0412(7) 0.0167(6) 0.0083(6) 0.0116(6) C3 0.0645(11) 0.0580(10) 0.0526(9) 0.0349(8) 0.0080(8) 0.0201(8) C4 0.0907(15) 0.0768(12) 0.0563(10) 0.0493(11) 0.0171(9) 0.0395(9) C5 0.0643(10) 0.0670(10) 0.0434(8) 0.0351(8) 0.0146(7) 0.0302(8) C6 0.0338(7) 0.0433(7) 0.0349(6) 0.0140(5) 0.0029(5) 0.0164(6) C7 0.0372(7) 0.0439(7) 0.0349(6) 0.0128(6) 0.0033(5) 0.0162(6) C8 0.0341(7) 0.0403(7) 0.0350(7) 0.0107(5) 0.0019(5) 0.0129(6) C9 0.0448(8) 0.0462(8) 0.0371(7) 0.0140(6) 0.0035(6) 0.0135(6) C10 0.0513(9) 0.0480(8) 0.0424(8) 0.0177(7) 0.0062(7) 0.0077(6) C11 0.0636(11) 0.0464(9) 0.0567(10) 0.0270(8) 0.0039(8) 0.0133(7) C12 0.0686(11) 0.0537(9) 0.0532(9) 0.0280(8) 0.0064(8) 0.0253(8) C13 0.0401(7) 0.0451(7) 0.0398(7) 0.0124(6) 0.0004(6) 0.0180(6) C14 0.0443(8) 0.0438(7) 0.0368(7) 0.0195(6) 0.0093(6) 0.0183(6) C15 0.0438(8) 0.0485(8) 0.0429(8) 0.0173(6) 0.0028(6) 0.0152(6) C16 0.0481(9) 0.0531(9) 0.0517(9) 0.0052(7) 0.0063(7) 0.0205(8) C17 0.0591(11) 0.0699(11) 0.0556(9) 0.0030(8) 0.0076(8) 0.0376(9) C18 0.0491(9) 0.0654(10) 0.0428(8) 0.0070(7) 0.0031(7) 0.0301(8) C19 0.0376(7) 0.0449(7) 0.0354(7) 0.0167(6) 0.0105(5) 0.0176(6) C20 0.0415(7) 0.0442(7) 0.0358(7) 0.0168(6) 0.0114(5) 0.0177(6) C21 0.0401(7) 0.0419(7) 0.0371(7) 0.0188(6) 0.0127(5) 0.0153(6) C22 0.0496(8) 0.0477(8) 0.0366(7) 0.0189(7) 0.0081(6) 0.0140(6) C23 0.0521(9) 0.0480(8) 0.0428(8) 0.0125(7) 0.0037(7) 0.0080(7) C24 0.0618(11) 0.0489(9) 0.0565(10) 0.0001(8) 0.0099(8) 0.0162(8) C25 0.0629(11) 0.0558(10) 0.0525(9) 0.0032(8) 0.0132(8) 0.0244(8) C26 0.0454(8) 0.0448(7) 0.0388(7) 0.0173(6) 0.0149(6) 0.0185(6) 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 C1 . 1.348(2) yes O2 C13 . 1.294(2) yes O3 C14 . 1.354(2) yes O4 C26 . 1.297(2) yes N1 C7 . 1.298(2) yes N1 C6 . 1.412(2) yes N2 C20 . 1.299(2) yes N2 C19 . 1.412(2) yes C1 C2 . 1.391(2) no C1 C6 . 1.403(2) no C2 C3 . 1.371(2) no C3 C4 . 1.386(3) no C4 C5 . 1.381(2) no C5 C6 . 1.382(2) no C7 C8 . 1.416(2) yes C8 C9 . 1.415(2) yes C8 C13 . 1.432(2) yes C9 C10 . 1.370(2) no C10 C11 . 1.393(3) no C11 C12 . 1.371(2) no C12 C13 . 1.415(2) yes C14 C15 . 1.385(2) no C14 C19 . 1.396(2) no C15 C16 . 1.381(2) no C16 C17 . 1.386(3) no C17 C18 . 1.382(2) no C18 C19 . 1.389(2) no C20 C21 . 1.410(2) yes C21 C22 . 1.410(2) yes C21 C26 . 1.438(2) yes C22 C23 . 1.361(2) no C23 C24 . 1.396(2) no C24 C25 . 1.372(3) no C25 C26 . 1.413(2) yes