#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011640.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011640 loop_ _publ_author_name 'Gloe, Karsten' 'Uzoukwu, Bieluonwu A.' 'Rademacher, Otto' '4-Acetyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazole-3-one hydrate' _publ_section_title ; 4-Acetyl-5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one hydrate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e580 _journal_page_last e581 _journal_volume 56 _journal_year 2000 _chemical_formula_iupac 'C12 H12 N2 O2, H2 O' _chemical_formula_moiety 'C12 H12 N2 O2, H2 O' _chemical_formula_sum 'C12 H14 N2 O3' _chemical_formula_weight 234.25 _chemical_melting_point 331 _chemical_name_systematic '4-Acetyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazole-3-one hydrate' _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method 'manuel editing of a SHELXL97.cif file' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.419(4) _cell_length_b 7.522(4) _cell_length_c 21.814(8) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.22 _cell_measurement_theta_min 19.77 _cell_volume 1217.3(10) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Nonius, 1992)' _computing_data_reduction 'XCAD4/PC (Harms, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator 'graphite ' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0434 _diffrn_reflns_av_sigmaI/netI .0258 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 2346 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 3.29 _diffrn_standards_decay_% 4 _diffrn_standards_interval_count 400 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .093 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 496 _exptl_crystal_size_max 1.0 _exptl_crystal_size_mid .58 _exptl_crystal_size_min .58 _refine_diff_density_max .161 _refine_diff_density_min -.125 _refine_ls_abs_structure_details 'not determined' _refine_ls_extinction_coef .016(3) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 1264 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all .042 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.06P)^2^+0.0872P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .103 _reflns_number_gt 1907 _reflns_number_total 2130 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qa0436.cif _[local]_cod_data_source_block I _cod_original_cell_volume 1217.2(10) _cod_database_code 2011640 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 C1 .3006(5) .6554(4) .80572(10) .0642(8) Uani d . 1 . . C H1A .3405 .5381 .8165 .096 Uiso calc R 1 . . H H1B .3926 .7139 .7822 .096 Uiso calc R 1 . . H H1C .1924 .6474 .7818 .096 Uiso calc R 1 . . H C2 .2640(4) .7595(3) .86275(9) .0442(6) Uani d . 1 . . C C3 .2065(3) .9329(3) .87092(10) .0450(6) Uani d . 1 . . C C4 .2025(3) .9646(3) .93560(10) .0405(5) Uani d . 1 . . C C5 .2472(3) .7556(3) 1.02564(9) .0403(5) Uani d . 1 . . C C6 .1852(3) .5886(3) 1.04159(11) .0473(6) Uani d . 1 . . C H6 .1477 .5087 1.0116 .057 Uiso calc R 1 . . H C7 .1801(4) .5423(4) 1.10320(11) .0580(7) Uani d . 1 . . C H7 .1403 .4299 1.1146 .070 Uiso calc R 1 . . H C8 .2335(4) .6613(4) 1.14730(12) .0653(8) Uani d . 1 . . C H8 .2286 .6293 1.1884 .078 Uiso calc R 1 . . H C9 .2936(4) .8261(4) 1.13119(11) .0607(8) Uani d . 1 . . C H9 .3289 .9059 1.1615 .073 Uiso calc R 1 . . H C10 .3027(3) .8759(3) 1.06971(11) .0492(6) Uani d . 1 . . C H10 .3452 .9877 1.0586 .059 Uiso calc R 1 . . H C11 .1504(4) 1.0539(3) .82234(12) .0619(8) Uani d . 1 . . C C12 .0708(6) 1.2292(4) .83890(14) .0762(10) Uani d . 1 . . C H12A .0403 1.2929 .8022 .114 Uiso calc R 1 . . H H12B .1568 1.2967 .8622 .114 Uiso calc R 1 . . H H12C -.0359 1.2110 .8630 .114 Uiso calc R 1 . . H O1 .1666(2) 1.1021(2) .96597(7) .0500(5) Uani d . 1 . . O O2 .1599(5) 1.0093(3) .76881(9) .1074(11) Uani d . 1 . . O O3 .4281(3) .3596(2) .93939(8) .0551(5) Uani d . 1 . . O N1 .2858(3) .6831(2) .91714(8) .0431(5) Uani d . 1 . . N N2 .2520(3) .8067(2) .96254(7) .0402(4) Uani d . 1 . . N H1 .337(4) .566(4) .9243(13) .061(8) Uiso d . 1 . . H H2 .367(5) .270(5) .9496(15) .085(11) Uiso d . 1 . . H H3 .490(7) .369(6) .9703(19) .125(17) 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 C1 .084(2) .0710(16) .0375(12) -.0125(16) .0015(14) -.0071(11) C2 .0458(12) .0538(12) .0330(11) -.0090(11) -.0040(11) .0038(10) C3 .0448(13) .0526(12) .0375(11) -.0109(10) -.0043(11) .0077(9) C4 .0368(12) .0463(11) .0384(11) -.0055(9) -.0020(11) .0046(9) C5 .0319(10) .0558(12) .0330(10) .0039(10) -.0024(10) .0044(9) C6 .0410(12) .0571(12) .0438(12) .0026(11) -.0011(11) .0087(11) C7 .0520(14) .0714(16) .0506(14) .0075(13) .0062(14) .0226(12) C8 .0590(16) .102(2) .0354(12) .0169(17) .0014(13) .0190(14) C9 .0562(17) .090(2) .0358(12) .0091(15) -.0074(13) -.0063(12) C10 .0456(13) .0632(13) .0387(12) .0011(11) -.0026(11) -.0016(11) C11 .0751(19) .0642(16) .0463(13) -.0182(14) -.0160(15) .0163(11) C12 .097(2) .0596(15) .0717(17) -.0058(18) -.033(2) .0198(14) O1 .0555(10) .0478(8) .0469(9) .0003(8) .0034(8) .0026(7) O2 .180(3) .1033(16) .0388(9) .009(2) -.0126(16) .0184(10) O3 .0647(11) .0487(10) .0520(10) -.0030(9) -.0091(10) .0012(8) N1 .0476(11) .0460(10) .0356(9) .0000(9) -.0015(9) .0004(8) N2 .0449(10) .0461(9) .0298(8) -.0011(9) .0001(8) .0010(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 C1 C2 . 1.495(3) yes C1 H1A . .9600 no C1 H1B . .9600 no C1 H1C . .9600 no C2 N1 . 1.328(3) yes C2 C3 . 1.384(3) yes C3 C4 . 1.431(3) yes C3 C11 . 1.458(3) yes C4 O1 . 1.256(3) yes C4 N2 . 1.376(3) yes C5 C6 . 1.382(3) no C5 C10 . 1.383(3) no C5 N2 . 1.430(3) yes C6 C7 . 1.389(3) no C6 H6 . .9300 no C7 C8 . 1.372(4) no C7 H7 . .9300 no C8 C9 . 1.363(4) no C8 H8 . .9300 no C9 C10 . 1.394(3) no C9 H9 . .9300 no C10 H10 . .9300 no C11 O2 . 1.217(3) yes C11 C12 . 1.489(4) yes C12 H12A . .9600 no C12 H12B . .9600 no C12 H12C . .9600 no O3 H2 . .84(4) no O3 H3 . .82(5) no N1 N2 . 1.381(3) yes N1 H1 . .97(3) no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 5 -1 -8 4 1 4 2 -5 3 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 H1A 109.5 no C2 C1 H1B 109.5 no H1A C1 H1B 109.5 no C2 C1 H1C 109.5 no H1A C1 H1C 109.5 no H1B C1 H1C 109.5 no N1 C2 C3 109.3(2) yes N1 C2 C1 119.7(2) yes C3 C2 C1 131.1(2) yes C2 C3 C4 106.9(2) no C2 C3 C11 125.7(2) no C4 C3 C11 127.3(2) no O1 C4 N2 122.8(2) yes O1 C4 C3 131.4(2) yes N2 C4 C3 105.75(19) yes C6 C5 C10 121.2(2) no C6 C5 N2 119.66(19) no C10 C5 N2 119.1(2) no C5 C6 C7 118.7(2) no C5 C6 H6 120.6 no C7 C6 H6 120.6 no C8 C7 C6 120.5(3) no C8 C7 H7 119.8 no C6 C7 H7 119.8 no C9 C8 C7 120.4(2) no C9 C8 H8 119.8 no C7 C8 H8 119.8 no C8 C9 C10 120.5(3) no C8 C9 H9 119.7 no C10 C9 H9 119.7 no C5 C10 C9 118.6(3) no C5 C10 H10 120.7 no C9 C10 H10 120.7 no O2 C11 C3 120.6(3) yes O2 C11 C12 120.0(3) yes C3 C11 C12 119.3(2) yes C11 C12 H12A 109.5 no C11 C12 H12B 109.5 no H12A C12 H12B 109.5 no C11 C12 H12C 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no H2 O3 H3 99(3) no C2 N1 N2 109.10(18) no C2 N1 H1 125.7(17) no N2 N1 H1 124.5(17) no C4 N2 N1 108.86(17) yes C4 N2 C5 129.56(18) yes N1 N2 C5 120.94(17) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag N1 C2 C3 C4 3.0(3) no C1 C2 C3 C4 -177.3(3) no N1 C2 C3 C11 -173.4(3) no C1 C2 C3 C11 6.3(4) no C2 C3 C4 O1 176.9(2) no C11 C3 C4 O1 -6.7(5) no C2 C3 C4 N2 -1.9(3) no C11 C3 C4 N2 174.4(2) no C10 C5 C6 C7 -.3(4) no N2 C5 C6 C7 -179.4(2) no C5 C6 C7 C8 .8(4) no C6 C7 C8 C9 -.5(4) no C7 C8 C9 C10 -.3(4) no C6 C5 C10 C9 -.5(4) no N2 C5 C10 C9 178.6(2) no C8 C9 C10 C5 .9(4) no C2 C3 C11 O2 -3.8(5) no C4 C3 C11 O2 -179.5(3) no C2 C3 C11 C12 172.6(3) no C4 C3 C11 C12 -3.1(4) no C3 C2 N1 N2 -3.0(3) no C1 C2 N1 N2 177.3(2) no O1 C4 N2 N1 -178.8(2) no C3 C4 N2 N1 .2(3) no O1 C4 N2 C5 10.5(4) no C3 C4 N2 C5 -170.5(2) no C2 N1 N2 C4 1.7(3) no C2 N1 N2 C5 173.4(2) no C6 C5 N2 C4 136.8(2) no C10 C5 N2 C4 -42.3(4) no C6 C5 N2 N1 -32.9(3) no C10 C5 N2 N1 147.9(2) no