#------------------------------------------------------------------------------ #$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $ #$Revision: 14 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2003024.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_2003024 _journal_name_full 'Acta Crystallographica, Section B' _journal_year 1998 _journal_volume B54 _journal_page_first 671 _journal_page_last 676 _publ_section_title ; 2-Phenyl-4-hydroxyphthalazin-1-one - a benzoannelated derivative of maleic hydrazide. ; loop_ _publ_author_name 'Becker, Dan' 'Botoshansky, Mark' 'Gasper, Noga' 'Herbstein, Frank H.' 'Karni, Miriam' _publ_section_synopsis ;The crystal structure of C~14~H~10~N~2~O~2~ has been determined at 293 K, and the hydrogen-bonding pattern compared with those in the related crystals maleic hydrazide (two polymorphs), dichloromaleic hydrazide and luminol. The measured dimensions of monoclinic maleic hydrazide have been compared with those obtained from an extensive series of high-level molecular orbital calculations. ; _chemical_name_systematic ; 2,3-dihydro-2-phenyl-1,4-phthalazinedione ; _chemical_name_common '2-phenyl-4-hydroxyphthalazin-1-one' _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 N2 O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_weight 238.24 _chemical_melting_point 214 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.083(4) _cell_length_b 18.854(6) _cell_length_c 10.760(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.29(3) _cell_angle_gamma 90.00 _cell_volume 2340.4(13) _cell_formula_units_Z 8 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 12.1 _cell_measurement_temperature 293(2) _exptl_crystal_description Cube _exptl_crystal_colour 'Light yellow' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_meas 1.350 _exptl_crystal_density_method 'flotation' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Philips PW 1100/20' _diffrn_measurement_method \w/2\q _diffrn_reflns_number 4356 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '120 min' _diffrn_standards_decay_% 0.6 _reflns_number_total 4126 _reflns_number_observed 2793 _reflns_observed_criterion >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_obs 0.0500 _refine_ls_wR_factor_all 0.1324 _refine_ls_wR_factor_obs 0.1131 _refine_ls_goodness_of_fit_all 1.009 _refine_ls_goodness_of_fit_obs 1.072 _refine_ls_restrained_S_all 1.009 _refine_ls_restrained_S_obs 1.072 _refine_ls_number_reflns 4126 _refine_ls_number_parameters 405 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.3521P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/esd_max -0.009 _refine_ls_shift/esd_mean 0.002 _refine_diff_density_max 0.13 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' ; PROCN (extensively modified version (Goldberg, 1990) of PROC (Hornstra & Stubbe, 1973)). ; ; ORTEP II (Johnson, 1976); TEXSAN 1.6 MSC (Molecular Structure Corporation, 1992) ; 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 N1A 0.05163(14) 0.64539(9) 0.4066(2) 0.0445(5) Uani d . 1 . N N2A 0.14819(15) 0.60655(9) 0.4766(2) 0.0460(5) Uani d . 1 . N N1B 0.57233(15) 0.56942(9) 0.8745(2) 0.0432(4) Uani d . 1 . N N2B 0.64527(15) 0.60613(9) 0.9793(2) 0.0455(5) Uani d . 1 . N O1A 0.23650(15) 0.49966(9) 0.5216(2) 0.0612(5) Uani d . 1 . O O2A -0.12259(15) 0.65880(9) 0.2566(2) 0.0742(6) Uani d . 1 . O O1B 0.6770(2) 0.70302(9) 1.1088(2) 0.0640(5) Uani d . 1 . O O2B 0.41012(14) 0.55690(9) 0.7047(2) 0.0652(5) Uani d . 1 . O C1A 0.0522(2) 0.50176(11) 0.3643(2) 0.0438(5) Uani d . 1 . C C2A 0.0537(2) 0.42852(13) 0.3429(3) 0.0545(6) Uani d . 1 . C C3A -0.0394(2) 0.39683(14) 0.2542(3) 0.0598(7) Uani d . 1 . C C4A -0.1340(2) 0.43710(14) 0.1852(3) 0.0607(7) Uani d . 1 . C C5A -0.1368(2) 0.50901(14) 0.2043(2) 0.0558(6) Uani d . 1 . C C6A -0.0429(2) 0.54207(11) 0.2946(2) 0.0459(5) Uani d . 1 . C C7A -0.0430(2) 0.61851(12) 0.3160(2) 0.0488(6) Uani d . 1 . C C8A 0.1465(2) 0.53912(12) 0.4556(2) 0.0453(5) Uani d . 1 . C C9A 0.0615(2) 0.72010(11) 0.4352(2) 0.0442(5) Uani d . 1 . C C10A -0.0186(2) 0.75298(13) 0.4849(2) 0.0525(6) Uani d . 1 . C C11A -0.0088(2) 0.82502(13) 0.5117(3) 0.0603(7) Uani d . 1 . C C12A 0.0806(3) 0.86329(14) 0.4885(3) 0.0643(7) Uani d . 1 . C C13A 0.1596(2) 0.83028(14) 0.4386(3) 0.0642(7) Uani d . 1 . C C14A 0.1509(2) 0.75839(13) 0.4116(2) 0.0531(6) Uani d . 1 . C C1B 0.5015(2) 0.69978(12) 0.9368(2) 0.0456(5) Uani d . 1 . C C2B 0.4651(2) 0.76493(13) 0.9728(3) 0.0560(6) Uani d . 1 . C C3B 0.3599(2) 0.79220(15) 0.9013(3) 0.0671(8) Uani d . 1 . C C4B 0.2909(2) 0.7563(2) 0.7921(3) 0.0675(8) Uani d . 1 . C C5B 0.3254(2) 0.69203(14) 0.7577(3) 0.0585(7) Uani d . 1 . C C6B 0.4311(2) 0.66270(12) 0.8306(2) 0.0454(5) Uani d . 1 . C C7B 0.4676(2) 0.59328(12) 0.7968(2) 0.0471(5) Uani d . 1 . C C8B 0.6098(2) 0.66673(11) 1.0073(2) 0.0454(5) Uani d . 1 . C C9B 0.6198(2) 0.50204(11) 0.8533(2) 0.0435(5) Uani d . 1 . C C10B 0.5545(2) 0.44071(13) 0.8403(3) 0.0569(6) Uani d . 1 . C C11B 0.6037(3) 0.37653(14) 0.8252(3) 0.0693(8) Uani d . 1 . C C12B 0.7171(3) 0.3730(2) 0.8246(3) 0.0721(8) Uani d . 1 . C C13B 0.7816(3) 0.4336(2) 0.8368(3) 0.0740(8) Uani d . 1 . C C14B 0.7329(2) 0.49883(14) 0.8505(3) 0.0607(7) Uani d . 1 . C HO1A 0.295(3) 0.5240(17) 0.586(4) 0.105(11) Uiso d . 1 . H HO1B 0.748(3) 0.6781(18) 1.152(4) 0.115(12) Uiso d . 1 . H H2A 0.122(2) 0.4000(13) 0.393(2) 0.064(7) Uiso d . 1 . H H3A -0.036(2) 0.3468(15) 0.245(3) 0.073(8) Uiso d . 1 . H H4A -0.198(2) 0.4162(12) 0.125(2) 0.059(7) Uiso d . 1 . H H5A -0.202(2) 0.5378(13) 0.158(2) 0.061(7) Uiso d . 1 . H H10A -0.082(2) 0.7273(13) 0.501(2) 0.062(7) Uiso d . 1 . H H11A -0.069(2) 0.8487(13) 0.544(3) 0.068(8) Uiso d . 1 . H H12A 0.083(2) 0.9145(15) 0.504(3) 0.076(8) Uiso d . 1 . H H13A 0.224(3) 0.8566(15) 0.421(3) 0.082(9) Uiso d . 1 . H H14A 0.206(2) 0.7336(13) 0.377(3) 0.064(7) Uiso d . 1 . H H2B 0.516(2) 0.7895(13) 1.052(3) 0.067(7) Uiso d . 1 . H H3B 0.341(2) 0.8356(14) 0.925(3) 0.065(8) Uiso d . 1 . H H4B 0.214(3) 0.7778(15) 0.746(3) 0.086(9) Uiso d . 1 . H H5B 0.281(2) 0.6652(15) 0.687(3) 0.080(9) Uiso d . 1 . H H10B 0.478(2) 0.4437(13) 0.848(3) 0.068(8) Uiso d . 1 . H H11B 0.559(2) 0.3332(15) 0.819(3) 0.076(8) Uiso d . 1 . H H12B 0.750(3) 0.3285(17) 0.816(3) 0.093(10) Uiso d . 1 . H H13B 0.860(3) 0.4344(15) 0.844(3) 0.081(9) Uiso d . 1 . H H14B 0.779(3) 0.5424(15) 0.858(3) 0.086(9) 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 N1A 0.0369(9) 0.0375(10) 0.0496(11) 0.0022(7) -0.0019(8) -0.0009(8) N2A 0.0390(10) 0.0422(10) 0.0463(11) 0.0050(8) -0.0037(8) -0.0016(8) N1B 0.0397(10) 0.0383(9) 0.0445(10) -0.0009(8) 0.0016(8) -0.0018(8) N2B 0.0395(10) 0.0402(10) 0.0473(11) 0.0014(8) -0.0018(8) -0.0033(8) O1A 0.0488(9) 0.0480(10) 0.0672(11) 0.0100(8) -0.0130(8) -0.0057(8) O2A 0.0578(11) 0.0539(10) 0.0814(13) 0.0076(9) -0.0246(10) -0.0046(9) O1B 0.0555(10) 0.0510(10) 0.0655(11) 0.0089(8) -0.0128(9) -0.0171(8) O2B 0.0564(10) 0.0584(10) 0.0614(11) -0.0047(8) -0.0123(9) -0.0069(9) C1A 0.0453(12) 0.0449(12) 0.0375(11) -0.0030(9) 0.0067(10) -0.0009(10) C2A 0.0561(15) 0.0453(13) 0.0562(15) -0.0023(11) 0.0075(12) -0.0011(11) C3A 0.070(2) 0.0452(15) 0.058(2) -0.0088(13) 0.0099(13) -0.0085(12) C4A 0.062(2) 0.056(2) 0.0530(15) -0.0161(13) -0.0009(13) -0.0070(12) C5A 0.0496(14) 0.054(2) 0.0509(14) -0.0059(12) -0.0042(11) -0.0033(12) C6A 0.0439(12) 0.0442(12) 0.0422(12) -0.0042(10) 0.0013(10) -0.0004(10) C7A 0.0368(12) 0.0491(13) 0.0495(13) 0.0013(10) -0.0040(10) 0.0015(10) C8A 0.0379(12) 0.0476(13) 0.0433(12) 0.0046(9) 0.0010(10) -0.0027(10) C9A 0.0391(11) 0.0395(12) 0.0434(12) 0.0008(9) -0.0038(9) -0.0006(9) C10A 0.0499(14) 0.0493(14) 0.0561(15) 0.0022(11) 0.0124(12) 0.0026(11) C11A 0.068(2) 0.0493(15) 0.061(2) 0.0108(13) 0.0143(13) -0.0042(12) C12A 0.077(2) 0.0391(14) 0.066(2) -0.0011(13) 0.0054(14) -0.0048(13) C13A 0.061(2) 0.049(2) 0.075(2) -0.0102(13) 0.0093(14) -0.0016(13) C14A 0.0461(13) 0.0515(14) 0.058(2) -0.0013(11) 0.0094(12) -0.0051(12) C1B 0.0408(12) 0.0436(12) 0.0491(13) 0.0016(9) 0.0084(10) 0.0062(10) C2B 0.0526(14) 0.0482(14) 0.062(2) 0.0048(11) 0.0093(13) 0.0002(12) C3B 0.063(2) 0.053(2) 0.083(2) 0.0192(14) 0.019(2) 0.0077(15) C4B 0.0475(15) 0.068(2) 0.079(2) 0.0149(13) 0.0077(14) 0.014(2) C5B 0.0442(14) 0.061(2) 0.062(2) 0.0038(12) 0.0022(12) 0.0083(13) C6B 0.0371(11) 0.0478(13) 0.0454(12) 0.0005(9) 0.0029(10) 0.0097(10) C7B 0.0407(12) 0.0491(13) 0.0424(12) -0.0056(10) -0.0015(10) 0.0065(10) C8B 0.0404(12) 0.0425(13) 0.0458(13) -0.0005(10) 0.0013(10) -0.0031(10) C9B 0.0500(13) 0.0401(12) 0.0369(11) -0.0017(10) 0.0075(10) 0.0005(9) C10B 0.064(2) 0.0442(14) 0.059(2) -0.0082(12) 0.0124(13) 0.0029(11) C11B 0.103(2) 0.0371(14) 0.063(2) -0.0083(15) 0.017(2) 0.0002(12) C12B 0.108(3) 0.049(2) 0.061(2) 0.019(2) 0.027(2) -0.0012(13) C13B 0.076(2) 0.067(2) 0.087(2) 0.015(2) 0.036(2) -0.001(2) C14B 0.061(2) 0.050(2) 0.075(2) -0.0006(12) 0.0264(14) 0.0004(13)