data_2200181 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o182 _journal_page_last o184 _publ_section_title ; 6-(2-Hydroxybenzoyl)-2-(4-nitrophenyl)pyrazolo[1,5-a]pyrimidine ; loop_ _publ_author_name 'Cannon, Debbie' 'Quesada, Antonio' 'Quiroga, Jairo' 'Insuasty, Braulio' 'Abonia, Rodrigo' "Mej\'ia, Diana" 'Cobo, Justo' 'Nogueras, Manuel' "S\'anchez, Adolfo" 'Low, John Nicolson' _chemical_formula_moiety 'C19 H12 N4 O4' _chemical_formula_sum 'C19 H12 N4 O4' _chemical_formula_weight 360.33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.5421(2) _cell_length_b 11.5858(5) _cell_length_c 23.8057(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1528.56(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(10) _exptl_crystal_density_diffrn 1.566 _diffrn_ambient_temperature 150.0(10) 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 N1 .4216(5) .2523(2) .38267(13) .0246(7) Uani d . 1 . . N C2 .2294(6) .2706(3) .41569(16) .0231(8) Uani d . 1 . . C C21 .2235(7) .3756(3) .45031(16) .0236(8) Uani d . 1 . . C C22 .4135(7) .4528(3) .44951(17) .0292(9) Uani d . 1 . . C C23 .4127(7) .5509(3) .48185(18) .0313(9) Uani d . 1 . . C C24 .2193(7) .5701(3) .51646(16) .0270(9) Uani d . 1 . . C N24 .2188(7) .6734(3) .55150(15) .0354(9) Uani d . 1 . . N O21 .3823(6) .7435(2) .54588(14) .0465(8) Uani d . 1 . . O O22 .0492(6) .6874(2) .58380(14) .0490(9) Uani d . 1 . . O C25 .0268(7) .4960(3) .51892(17) .0299(9) Uani d . 1 . . C C26 .0278(6) .3979(3) .48571(16) .0261(8) Uani d . 1 . . C C3 .0589(6) .1814(3) .41285(16) .0242(8) Uani d . 1 . . C C3A .1556(6) .1025(3) .37594(16) .0235(8) Uani d . 1 . . C N4 .0807(6) -.0027(2) .35731(14) .0267(8) Uani d . 1 . . N C5 .2270(7) -.0559(3) .32334(16) .0270(9) Uani d . 1 . . C C6 .4488(7) -.0104(3) .30287(17) .0260(9) Uani d . 1 . . C C67 .6017(6) -.0860(3) .26614(17) .0274(9) Uani d . 1 . . C O67 .5901(5) -.1918(2) .27446(13) .0364(7) Uani d . 1 . . O C61 .7653(6) -.0379(3) .22383(16) .0244(9) Uani d . 1 . . C C62 .9607(7) -.1058(3) .20466(16) .0261(9) Uani d . 1 . . C O62 .9951(5) -.21614(19) .22193(11) .0292(6) Uani d . 1 . . O C63 1.1303(7) -.0592(3) .16808(16) .0295(9) Uani d . 1 . . C C64 1.0969(7) .0512(3) .14697(17) .0312(9) Uani d . 1 . . C C65 .8972(8) .1152(3) .16177(17) .0324(10) Uani d . 1 . . C C66 .7353(7) .0720(3) .20037(16) .0284(9) Uani d . 1 . . C C7 .5201(7) .0945(3) .32124(15) .0241(8) Uani d . 1 . . C N7A .3740(5) .1493(2) .35832(13) .0227(7) Uani d . 1 . . N H22 .5483 .4376 .4260 .035 Uiso calc R 1 . . H H23 .5428 .6042 .4803 .038 Uiso calc R 1 . . H H25 -.1055 .5118 .5431 .036 Uiso calc R 1 . . H H26 -.1044 .3457 .4870 .031 Uiso calc R 1 . . H H3 -.0907 .1765 .4322 .029 Uiso calc R 1 . . H H5 .1824 -.1310 .3112 .032 Uiso calc R 1 . . H H62 .8597 -.2375 .2399 .035 Uiso d R 1 . . H H63 1.2683 -.1028 .1576 .035 Uiso calc R 1 . . H H64 1.2130 .0831 .1220 .037 Uiso calc R 1 . . H H65 .8711 .1889 .1454 .039 Uiso calc R 1 . . H H66 .6009 .1177 .2113 .034 Uiso calc R 1 . . H H7 .6666 .1285 .3087 .029 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 N1 .0256(16) .0248(16) .0234(17) .0000(13) .0001(15) -.0026(15) C2 .0191(18) .030(2) .0200(19) -.0002(15) -.0006(17) .0047(17) C21 .0227(19) .024(2) .024(2) .0025(15) .0004(17) .0001(16) C22 .026(2) .031(2) .031(2) -.0024(17) .0068(18) -.0041(19) C23 .028(2) .031(2) .035(2) -.0028(17) .000(2) .000(2) C24 .032(2) .026(2) .023(2) .0011(17) -.0002(18) .0008(18) N24 .044(2) .037(2) .0248(19) .0028(18) .0022(19) -.0056(17) O21 .0533(19) .0376(17) .049(2) -.0140(16) .0074(17) -.0150(16) O22 .064(2) .0443(18) .0391(19) .0021(16) .0189(19) -.0096(15) C25 .030(2) .034(2) .025(2) .0036(18) .0060(18) .0030(19) C26 .0226(18) .029(2) .026(2) -.0028(17) .0020(17) .0010(18) C3 .0219(18) .031(2) .020(2) -.0003(16) .0001(17) .0012(17) C3A .0190(18) .028(2) .023(2) .0011(15) -.0028(16) .0037(19) N4 .0250(16) .0268(17) .0282(19) -.0032(14) -.0016(15) -.0020(15) C5 .028(2) .027(2) .026(2) -.0041(17) -.0028(18) -.0009(17) C6 .0273(19) .024(2) .026(2) -.0001(16) .0025(18) .0008(17) C67 .025(2) .029(2) .028(2) .0009(17) -.0043(17) -.0038(17) O67 .0444(17) .0226(14) .0423(19) -.0017(13) .0068(15) -.0004(13) C61 .0216(18) .028(2) .023(2) .0006(16) .0005(18) -.0033(17) C62 .0297(19) .023(2) .025(2) .0008(16) -.0075(17) -.0054(17) O62 .0362(15) .0234(13) .0281(15) .0051(11) .0010(14) -.0003(12) C63 .028(2) .035(2) .026(2) .0050(18) .0034(18) -.0044(19) C64 .037(2) .031(2) .026(2) -.0025(18) .0044(19) -.0040(19) C65 .046(2) .025(2) .027(2) .0009(19) .003(2) .0006(18) C66 .034(2) .027(2) .025(2) .0059(17) -.0038(19) -.0054(17) C7 .0209(18) .028(2) .023(2) .0006(16) .0021(16) .0020(16) N7A .0208(15) .0235(16) .0237(17) -.0009(13) .0001(14) .0008(14) 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 N1 C2 . 1.341(5) yes N1 N7A . 1.353(4) yes C2 C3 . 1.402(5) no C2 C21 . 1.470(5) no C21 C22 . 1.382(5) no C21 C26 . 1.397(5) no C22 C23 . 1.373(5) no C22 H22 . .9500 no C23 C24 . 1.370(5) no C23 H23 . .9500 no C24 C25 . 1.371(5) no C24 N24 . 1.460(5) yes N24 O21 . 1.224(4) no N24 O22 . 1.225(4) no C25 C26 . 1.385(5) no C25 H25 . .9500 no C26 H26 . .9500 no C3 C3A . 1.377(5) no C3 H3 . .9500 no C3A N4 . 1.362(5) yes C3A N7A . 1.391(5) yes N4 C5 . 1.300(5) no C5 C6 . 1.424(5) no C5 H5 . .9500 no C6 C7 . 1.351(5) no C6 C67 . 1.500(5) no C67 O67 . 1.244(4) no C67 C61 . 1.465(5) no C61 C66 . 1.401(5) no C61 C62 . 1.415(5) no C62 O62 . 1.356(4) no C62 C63 . 1.390(5) no O62 H62 . .8980 no C63 C64 . 1.387(6) no C63 H63 . .9500 no C64 C65 . 1.377(5) no C64 H64 . .9500 no C65 C66 . 1.378(5) no C65 H65 . .9500 no C66 H66 . .9500 no C7 N7A . 1.356(5) yes C7 H7 . .9500 no