#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/88/2008880.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_2008880 loop_ _publ_author_name 'Benniston, Andrew C.' 'Yufit, D. S.' 'Howard, Judith A. K.' _publ_section_title ; Bis(hydrazinium) 4-hydroxy-1-oxo-2H-phthalazine-6,7-dicarboxylate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1535 _journal_page_last 1536 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac '2N2 H5 1+, C10 H4 N2 O6 2-' _chemical_formula_moiety '2N2 H5 1+, C10 H4 N2 O6 2-' _chemical_formula_sum 'C10 H14 N6 O6' _chemical_formula_weight 314.27 _chemical_name_systematic ; 4-Hydroxy-1-oxo-2H-phthalazine-6,7-dicarboxylate bis-hydrazinium ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 113.62(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 25.300(5) _cell_length_b 7.366(2) _cell_length_c 14.609(3) _cell_measurement_reflns_used 606 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 20.8 _cell_measurement_theta_min 10.2 _cell_volume 2494.4(11) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics SHELX97 _computing_publication_material SHELX97 _computing_structure_refinement SHELX97 _computing_structure_solution 'SHELX97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 14694 _diffrn_reflns_theta_full 29.96 _diffrn_reflns_theta_max 29.96 _diffrn_reflns_theta_min 1.76 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1312 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.392 _refine_diff_density_min -0.285 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 3496 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.077 _refine_ls_R_factor_gt 0.044 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.05P)^2^+1.50P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.107 _reflns_number_gt 2443 _reflns_number_total 3496 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf1312.cif _[local]_cod_data_source_block cf1312 _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_original_cell_volume 2494.4(9) _cod_database_code 2008880 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 O1 -0.00189(5) 0.5182(2) 0.12520(10) 0.0230(3) Uani d . 1 . . O O2 -0.05768(5) 1.2197(2) 0.03852(8) 0.0153(3) Uani d . 1 . . O O3 0.17570(5) 1.2165(2) 0.41534(8) 0.0158(3) Uani d . 1 . . O O4 0.16636(5) 1.3441(2) 0.27091(8) 0.0202(3) Uani d . 1 . . O O5 0.22221(5) 0.8840(2) 0.33606(8) 0.0158(3) Uani d . 1 . . O O6 0.18374(5) 0.7343(2) 0.42841(8) 0.0163(3) Uani d . 1 . . O N2 -0.06634(6) 0.7360(2) 0.03480(10) 0.0131(3) Uani d . 1 . . N N3 -0.07722(6) 0.9196(2) 0.01880(10) 0.0125(3) Uani d . 1 . . N C1 -0.01663(7) 0.6922(2) 0.10370(10) 0.0132(3) Uani d . 1 . . C C4 -0.04189(6) 1.0598(2) 0.06450(10) 0.0119(3) Uani d . 1 . . C C5 0.05651(7) 1.1380(2) 0.19340(10) 0.0120(3) Uani d . 1 . . C C6 0.10950(6) 1.0835(2) 0.26440(10) 0.0108(3) Uani d . 1 . . C C7 0.12111(6) 0.8976(2) 0.28580(10) 0.0107(3) Uani d . 1 . . C C8 0.07984(7) 0.7683(2) 0.23590(10) 0.0122(3) Uani d . 1 . . C C9 0.02650(6) 0.8227(2) 0.16220(10) 0.0115(3) Uani d . 1 . . C C10 0.01443(6) 1.0079(2) 0.14180(10) 0.0111(3) Uani d . 1 . . C C11 0.15408(6) 1.2256(2) 0.32110(10) 0.0120(3) Uani d . 1 . . C C12 0.18035(7) 0.8343(2) 0.35720(10) 0.0116(3) Uani d . 1 . . C N1S -0.19450(6) 0.9460(2) -0.13580(10) 0.0155(3) Uani d . 1 . . N N2S -0.23278(6) 1.0031(2) -0.08900(10) 0.0148(3) Uani d . 1 . . N N3S 0.16132(6) 0.3690(2) 0.62170(10) 0.0175(3) Uani d . 1 . . N N4S 0.16930(6) 0.4841(2) 0.54740(10) 0.0144(3) Uani d . 1 . . N H1O -0.0250(10) 0.444(4) 0.090(2) 0.051(8) Uiso d . 1 . . H H3N -0.1100(10) 0.944(3) -0.024(2) 0.025(6) Uiso d . 1 . . H H5 0.0487(9) 1.261(3) 0.1800(10) 0.021(5) Uiso d . 1 . . H H8 0.0874(8) 0.643(3) 0.2500(10) 0.017(5) Uiso d . 1 . . H H11S -0.1990(10) 1.028(3) -0.183(2) 0.036(6) Uiso d . 1 . . H H12S -0.2110(10) 0.848(3) -0.169(2) 0.030(6) Uiso d . 1 . . H H21S -0.2670(10) 1.063(3) -0.137(2) 0.034(6) Uiso d . 1 . . H H22S -0.2450(10) 0.898(3) -0.060(2) 0.043(7) Uiso d . 1 . . H H23S -0.2125(9) 1.090(3) -0.035(2) 0.030(6) Uiso d . 1 . . H H31S 0.1255(9) 0.314(3) 0.5880(10) 0.020(5) Uiso d . 1 . . H H32S 0.1590(10) 0.448(3) 0.670(2) 0.031(6) Uiso d . 1 . . H H41S 0.1697(9) 0.403(3) 0.496(2) 0.028(6) Uiso d . 1 . . H H42S 0.1400(10) 0.575(3) 0.522(2) 0.032(6) Uiso d . 1 . . H H43S 0.2070(10) 0.540(3) 0.580(2) 0.030(6) 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 0.0166(6) 0.0093(6) 0.0287(7) -0.0006(5) -0.0060(5) -0.0021(5) O2 0.0129(5) 0.0114(6) 0.0161(6) 0.0001(4) 0.0000(4) 0.0016(4) O3 0.0175(6) 0.0153(6) 0.0115(5) -0.0015(5) 0.0024(5) -0.0013(4) O4 0.0197(6) 0.0194(6) 0.0165(6) -0.0069(5) 0.0020(5) 0.0032(5) O5 0.0117(5) 0.0190(6) 0.0151(6) -0.0004(5) 0.0036(4) 0.0011(5) O6 0.0142(5) 0.0170(6) 0.0146(6) 0.0009(5) 0.0025(4) 0.0042(5) N2 0.0123(6) 0.0107(6) 0.0142(6) 0.0006(5) 0.0030(5) 0.0000(5) N3 0.0099(6) 0.0103(6) 0.0134(6) 0.0010(5) 0.0005(5) 0.0010(5) C1 0.0119(7) 0.0116(8) 0.0141(7) -0.0009(6) 0.0031(6) -0.0010(6) C4 0.0100(7) 0.0150(8) 0.0100(7) 0.0004(6) 0.0032(6) 0.0002(6) C5 0.0127(7) 0.0107(8) 0.0119(7) 0.0000(6) 0.0041(6) 0.0005(6) C6 0.0118(7) 0.0119(7) 0.0088(7) -0.0016(6) 0.0044(6) -0.0008(6) C7 0.0099(7) 0.0129(8) 0.0091(7) 0.0009(6) 0.0034(6) -0.0001(6) C8 0.0120(7) 0.0113(8) 0.0122(7) 0.0008(6) 0.0037(6) 0.0003(6) C9 0.0111(7) 0.0115(7) 0.0120(7) 0.0002(6) 0.0046(6) 0.0000(6) C10 0.0104(6) 0.0128(8) 0.0095(7) 0.0013(6) 0.0032(6) -0.0001(6) C11 0.0086(7) 0.0119(7) 0.0135(7) 0.0004(6) 0.0021(6) -0.0010(6) C12 0.0106(7) 0.0107(7) 0.0109(7) 0.0000(6) 0.0017(6) -0.0031(6) N1S 0.0146(6) 0.0167(7) 0.0148(7) -0.0003(6) 0.0056(6) 0.0004(6) N2S 0.0127(6) 0.0155(7) 0.0144(7) 0.0010(6) 0.0035(5) -0.0010(6) N3S 0.0202(7) 0.0169(7) 0.0144(7) -0.0056(6) 0.0057(6) 0.0008(6) N4S 0.0140(6) 0.0136(7) 0.0135(7) -0.0003(6) 0.0034(5) 0.0015(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 . 1.336(2) ? O2 C4 . 1.253(2) ? O3 C11 . 1.264(2) ? O4 C11 . 1.256(2) ? O5 C12 . 1.270(2) ? O6 C12 . 1.249(2) ? N2 C1 . 1.298(2) ? N2 N3 . 1.381(2) ? N3 C4 . 1.354(2) ? C1 C9 . 1.449(2) ? C4 C10 . 1.470(2) ? C5 C6 . 1.386(2) ? C5 C10 . 1.406(2) ? C6 C7 . 1.409(2) ? C6 C11 . 1.518(2) ? C7 C8 . 1.385(2) ? C7 C12 . 1.516(2) ? C8 C9 . 1.406(2) ? C9 C10 . 1.404(2) ? N1S N2S . 1.454(2) ? N3S N4S . 1.454(2) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N2 N3 116.10(10) C4 N3 N2 128.00(10) N2 C1 O1 120.90(10) N2 C1 C9 124.0(2) O1 C1 C9 115.10(10) O2 C4 N3 120.00(10) O2 C4 C10 124.80(10) N3 C4 C10 115.20(10) C6 C5 C10 120.1(2) C5 C6 C7 120.00(10) C5 C6 C11 119.60(10) C7 C6 C11 120.40(10) C8 C7 C6 120.40(10) C8 C7 C12 118.70(10) C6 C7 C12 120.80(10) C7 C8 C9 119.8(2) C10 C9 C8 120.00(10) C10 C9 C1 118.10(10) C8 C9 C1 121.9(2) C9 C10 C5 119.60(10) C9 C10 C4 118.50(10) C5 C10 C4 121.8(2) O4 C11 O3 124.9(2) O4 C11 C6 117.70(10) O3 C11 C6 117.40(10) O6 C12 O5 125.90(10) O6 C12 C7 118.30(10) O5 C12 C7 115.70(10) _journal_paper_doi 10.1107/S0108270199007635