data_2014341 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2006 _journal_volume 62 _journal_page_first m37 _journal_page_last m40 _publ_section_title ; Disodium 2,5-dianilinoterephthalate decahydrate, an intermediate in the industrial synthesis of quinacridone pigments ; loop_ _publ_author_name 'Schmidt, Martin U.' 'Schmiermund, Torsten' 'Bolte, Michael' _chemical_formula_moiety '2Na +, C20 H14 N2 O4 2-, 10H2 O1' _chemical_formula_sum 'C20 H34 N2 Na2 O14' _chemical_formula_weight 572.47 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7638(7) _cell_length_b 12.4371(10) _cell_length_c 13.5720(11) _cell_angle_alpha 110.550(6) _cell_angle_beta 97.483(7) _cell_angle_gamma 101.857(6) _cell_volume 1322.14(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _exptl_crystal_density_diffrn 1.438 _diffrn_ambient_temperature 173(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 Na1 0.53040(8) 0.26076(6) 1.00816(5) 0.01921(17) Uani d . 1 . . Na Na2 0.11567(9) 0.18887(7) 0.92297(6) 0.02589(19) Uani d . 1 . . Na O1 0.68370(17) 0.10616(13) 1.00759(11) 0.0272(3) Uani d D 1 . . O H1A 0.638(3) 0.059(2) 0.9435(12) 0.063(10) Uiso d D 1 . . H H1B 0.7835(12) 0.127(2) 1.015(2) 0.047(8) Uiso d D 1 . . H O2 0.61030(15) 0.25796(12) 0.84887(10) 0.0211(3) Uani d D 1 . . O H2A 0.601(3) 0.3141(14) 0.8287(19) 0.037(7) Uiso d D 1 . . H H2B 0.565(3) 0.1911(10) 0.7992(15) 0.037(7) Uiso d D 1 . . H O3 0.41397(17) 0.25111(11) 1.15494(10) 0.0232(3) Uani d D 1 . . O H3A 0.420(3) 0.1970(14) 1.1779(18) 0.036(7) Uiso d D 1 . . H H3B 0.455(3) 0.3194(10) 1.2043(15) 0.041(7) Uiso d D 1 . . H O4 0.69974(15) 0.45652(12) 1.11449(10) 0.0226(3) Uani d D 1 . . O H4A 0.658(3) 0.465(3) 1.1683(15) 0.056(9) Uiso d D 1 . . H H4B 0.7989(12) 0.465(2) 1.1320(19) 0.037(7) Uiso d D 1 . . H O5 0.32948(16) 0.37672(11) 0.99626(10) 0.0212(3) Uani d D 1 . . O H5A 0.349(3) 0.4215(19) 1.0624(8) 0.047(8) Uiso d D 1 . . H H5B 0.322(3) 0.4160(19) 0.9573(15) 0.035(7) Uiso d D 1 . . H O6 0.32014(15) 0.08084(11) 0.89872(10) 0.0203(3) Uani d D 1 . . O H6A 0.347(3) 0.061(2) 0.8389(13) 0.047(8) Uiso d D 1 . . H H6B 0.320(3) 0.0281(19) 0.9242(19) 0.044(8) Uiso d D 1 . . H O7 0.09037(19) 0.22157(14) 1.10965(12) 0.0343(3) Uani d D 1 . . O H7B 0.1895(14) 0.236(3) 1.133(2) 0.049(8) Uiso d D 1 . . H O8 -0.07510(18) 0.00806(14) 0.87289(14) 0.0355(4) Uani d D 1 . . O H8A -0.048(3) -0.048(2) 0.886(3) 0.079(12) Uiso d D 1 . . H H8B -0.1679(17) -0.014(2) 0.8340(19) 0.039(7) Uiso d D 1 . . H O9 -0.05840(17) 0.30603(14) 0.91775(13) 0.0309(3) Uani d D 1 . . O H9A -0.029(4) 0.359(3) 0.893(4) 0.118(18) Uiso d D 1 . . H H9B -0.1598(12) 0.284(2) 0.904(2) 0.046(8) Uiso d D 1 . . H O1W 0.03178(17) 0.48841(14) 0.13037(12) 0.0307(3) Uani d D 1 . . O H1WA 0.1278(17) 0.508(3) 0.166(2) 0.052(8) Uiso d D 1 . . H H1WB 0.012(4) 0.424(2) 0.076(2) 0.121(18) Uiso d D 1 . . H C1 0.49982(19) 0.84814(14) 0.59739(12) 0.0138(3) Uani d . 1 . . C C2 0.39469(19) 0.83052(14) 0.50050(13) 0.0143(3) Uani d . 1 . . C C3 0.39014(19) 0.73286(14) 0.40676(13) 0.0149(3) Uani d . 1 . . C H3 0.3189 0.7194 0.3419 0.018 Uiso calc R 1 . . H C4 0.48525(18) 0.65437(14) 0.40403(12) 0.0133(3) Uani d . 1 . . C C5 0.59294(19) 0.67363(14) 0.50066(13) 0.0145(3) Uani d . 1 . . C C6 0.59442(19) 0.76949(14) 0.59452(13) 0.0148(3) Uani d . 1 . . C H6 0.6635 0.7817 0.6598 0.018 Uiso calc R 1 . . H C11 0.51197(19) 0.94655(14) 0.70528(13) 0.0147(3) Uani d . 1 . . C O11 0.44370(16) 1.02777(11) 0.70804(10) 0.0214(3) Uani d . 1 . . O O12 0.58942(16) 0.94275(11) 0.78949(9) 0.0210(3) Uani d . 1 . . O N21 0.30325(17) 0.90888(13) 0.49500(12) 0.0186(3) Uani d . 1 . . N H21 0.325(3) 0.978(2) 0.554(2) 0.029(6) Uiso d . 1 . . H C21 0.15037(19) 0.87519(15) 0.42758(13) 0.0158(3) Uani d . 1 . . C C22 0.0993(2) 0.95982(18) 0.39655(18) 0.0279(4) Uani d . 1 . . C H22 0.1709 1.0362 0.4157 0.033 Uiso calc R 1 . . H C23 -0.0563(2) 0.93346(19) 0.33745(19) 0.0313(5) Uani d . 1 . . C H23 -0.0900 0.9925 0.3179 0.038 Uiso calc R 1 . . H C24 -0.1618(2) 0.82185(18) 0.30719(15) 0.0249(4) Uani d . 1 . . C H24 -0.2674 0.8039 0.2668 0.030 Uiso calc R 1 . . H C25 -0.1108(2) 0.73690(17) 0.33681(17) 0.0273(4) Uani d . 1 . . C H25 -0.1822 0.6602 0.3164 0.033 Uiso calc R 1 . . H C26 0.0433(2) 0.76245(16) 0.39595(16) 0.0230(4) Uani d . 1 . . C H26 0.0763 0.7029 0.4151 0.028 Uiso calc R 1 . . H C41 0.46847(19) 0.55337(14) 0.29684(13) 0.0146(3) Uani d . 1 . . C O41 0.55209(15) 0.48038(11) 0.29349(10) 0.0202(3) Uani d . 1 . . O O42 0.37382(15) 0.54691(11) 0.21424(10) 0.0209(3) Uani d . 1 . . O N51 0.68861(18) 0.59750(13) 0.50526(12) 0.0188(3) Uani d . 1 . . N H51 0.661(3) 0.526(3) 0.450(2) 0.036(7) Uiso d . 1 . . H C51 0.83863(19) 0.62940(15) 0.57529(13) 0.0155(3) Uani d . 1 . . C C52 0.9415(2) 0.74526(17) 0.62019(16) 0.0255(4) Uani d . 1 . . C H52 0.9076 0.8081 0.6078 0.031 Uiso calc R 1 . . H C53 1.0926(2) 0.76896(18) 0.68275(18) 0.0305(4) Uani d . 1 . . C H53 1.1606 0.8480 0.7127 0.037 Uiso calc R 1 . . H C54 1.1457(2) 0.67906(19) 0.70221(16) 0.0271(4) Uani d . 1 . . C H54 1.2492 0.6958 0.7450 0.032 Uiso calc R 1 . . H C55 1.0444(2) 0.56394(18) 0.65779(16) 0.0265(4) Uani d . 1 . . C H55 1.0796 0.5014 0.6699 0.032 Uiso calc R 1 . . H C56 0.8916(2) 0.53892(16) 0.59562(15) 0.0218(4) Uani d . 1 . . C H56 0.8233 0.4600 0.5670 0.026 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 Na1 0.0218(3) 0.0168(3) 0.0137(3) 0.0013(3) 0.0035(3) 0.0021(3) Na2 0.0222(4) 0.0216(4) 0.0316(4) 0.0048(3) 0.0068(3) 0.0080(3) O1 0.0288(7) 0.0285(7) 0.0182(6) 0.0071(6) 0.0033(5) 0.0030(6) O2 0.0252(6) 0.0179(6) 0.0154(6) 0.0009(5) 0.0020(5) 0.0047(5) O3 0.0352(7) 0.0146(6) 0.0168(6) 0.0038(5) 0.0052(5) 0.0046(5) O4 0.0197(6) 0.0248(7) 0.0171(6) 0.0024(5) 0.0027(5) 0.0036(5) O5 0.0255(6) 0.0182(6) 0.0163(6) 0.0043(5) 0.0022(5) 0.0041(5) O6 0.0224(6) 0.0183(6) 0.0168(6) 0.0048(5) 0.0039(5) 0.0032(5) O7 0.0368(8) 0.0353(8) 0.0273(7) 0.0059(7) 0.0008(6) 0.0124(6) O8 0.0250(7) 0.0277(8) 0.0467(9) 0.0002(6) -0.0024(6) 0.0137(7) O9 0.0231(7) 0.0291(8) 0.0373(8) 0.0058(6) -0.0004(6) 0.0121(6) O1W 0.0234(7) 0.0367(8) 0.0284(7) 0.0053(6) 0.0035(6) 0.0110(7) C1 0.0149(7) 0.0112(7) 0.0112(7) 0.0012(6) 0.0020(6) 0.0013(6) C2 0.0142(7) 0.0125(7) 0.0146(7) 0.0036(6) 0.0016(6) 0.0039(6) C3 0.0149(7) 0.0159(8) 0.0105(7) 0.0026(6) -0.0009(6) 0.0031(6) C4 0.0137(7) 0.0126(7) 0.0110(7) 0.0026(6) 0.0025(5) 0.0019(6) C5 0.0143(7) 0.0123(7) 0.0142(7) 0.0024(6) 0.0012(6) 0.0032(6) C6 0.0166(7) 0.0144(7) 0.0102(7) 0.0035(6) -0.0010(6) 0.0027(6) C11 0.0160(7) 0.0124(7) 0.0119(7) 0.0026(6) 0.0019(6) 0.0013(6) O11 0.0273(6) 0.0164(6) 0.0151(6) 0.0099(5) -0.0001(5) -0.0007(5) O12 0.0294(7) 0.0189(6) 0.0107(5) 0.0086(5) -0.0001(5) 0.0015(5) N21 0.0195(7) 0.0133(7) 0.0160(7) 0.0068(6) -0.0037(5) -0.0011(6) C21 0.0164(7) 0.0173(8) 0.0122(7) 0.0063(6) 0.0016(6) 0.0036(6) C22 0.0207(9) 0.0217(9) 0.0412(11) 0.0010(7) -0.0039(8) 0.0188(9) C23 0.0227(9) 0.0316(11) 0.0445(12) 0.0070(8) -0.0039(8) 0.0247(10) C24 0.0178(8) 0.0286(10) 0.0239(9) 0.0059(7) -0.0032(7) 0.0078(8) C25 0.0192(9) 0.0189(9) 0.0356(11) 0.0017(7) 0.0003(7) 0.0050(8) C26 0.0206(8) 0.0160(8) 0.0308(10) 0.0057(7) 0.0015(7) 0.0083(7) C41 0.0153(7) 0.0130(7) 0.0117(7) 0.0011(6) 0.0026(6) 0.0019(6) O41 0.0245(6) 0.0165(6) 0.0151(6) 0.0098(5) 0.0008(5) -0.0003(5) O42 0.0255(6) 0.0193(6) 0.0118(5) 0.0070(5) -0.0020(5) 0.0006(5) N51 0.0197(7) 0.0143(7) 0.0163(7) 0.0074(6) -0.0028(6) -0.0002(6) C51 0.0165(7) 0.0182(8) 0.0108(7) 0.0060(6) 0.0020(6) 0.0040(6) C52 0.0233(9) 0.0166(8) 0.0323(10) 0.0056(7) -0.0025(7) 0.0073(7) C53 0.0231(9) 0.0197(9) 0.0378(11) 0.0011(7) -0.0049(8) 0.0053(8) C54 0.0195(8) 0.0306(10) 0.0253(9) 0.0059(7) -0.0054(7) 0.0082(8) C55 0.0258(9) 0.0269(10) 0.0294(10) 0.0095(8) -0.0012(7) 0.0152(8) C56 0.0223(8) 0.0172(8) 0.0249(9) 0.0036(7) 0.0002(7) 0.0096(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 Na1 O2 . 2.3487(14) ? Na1 O3 . 2.3815(15) ? Na1 O4 . 2.3882(15) ? Na1 O6 . 2.4224(14) ? Na1 O5 . 2.5178(15) ? Na1 O1 . 2.5605(17) ? Na1 Na2 . 3.4915(11) ? Na1 H4A . 2.60(3) ? Na2 O8 . 2.3237(16) ? Na2 O9 . 2.3266(17) ? Na2 O6 . 2.4407(15) ? Na2 O5 . 2.4582(15) ? Na2 O7 . 2.4685(18) ? Na2 H7B . 2.66(3) ? O1 H1A . 0.846(10) ? O1 H1B . 0.841(10) ? O2 H2A . 0.85(2) ? O2 H2B . 0.840(9) ? O3 H3A . 0.84(2) ? O3 H3B . 0.844(10) ? O4 H4A . 0.845(10) ? O4 H4B . 0.845(10) ? O5 H5A . 0.846(10) ? O5 H5B . 0.84(2) ? O6 H6A . 0.844(10) ? O6 H6B . 0.84(3) ? O7 H7B . 0.843(10) ? O8 H8A . 0.85(3) ? O8 H8B . 0.843(10) ? O9 H9A . 0.85(4) ? O9 H9B . 0.849(10) ? O1W H1WA . 0.851(10) ? O1W H1WB . 0.84(3) ? C1 C6 . 1.400(2) ? C1 C2 . 1.423(2) ? C1 C11 . 1.517(2) ? C2 N21 . 1.398(2) ? C2 C3 . 1.406(2) ? C3 C4 . 1.402(2) ? C3 H3 . 0.9500 ? C4 C5 . 1.426(2) ? C4 C41 . 1.517(2) ? C5 N51 . 1.399(2) ? C5 C6 . 1.403(2) ? C6 H6 . 0.9500 ? C11 O11 . 1.268(2) ? C11 O12 . 1.272(2) ? N21 C21 . 1.410(2) ? N21 H21 . 0.91(3) ? C21 C22 . 1.393(2) ? C21 C26 . 1.401(2) ? C22 C23 . 1.399(3) ? C22 H22 . 0.9500 ? C23 C24 . 1.387(3) ? C23 H23 . 0.9500 ? C24 C25 . 1.387(3) ? C24 H24 . 0.9500 ? C25 C26 . 1.390(3) ? C25 H25 . 0.9500 ? C26 H26 . 0.9500 ? C41 O41 . 1.271(2) ? C41 O42 . 1.272(2) ? N51 C51 . 1.409(2) ? N51 H51 . 0.90(3) ? C51 C56 . 1.399(2) ? C51 C52 . 1.402(2) ? C52 C53 . 1.390(3) ? C52 H52 . 0.9500 ? C53 C54 . 1.388(3) ? C53 H53 . 0.9500 ? C54 C55 . 1.391(3) ? C54 H54 . 0.9500 ? C55 C56 . 1.397(3) ? C55 H55 . 0.9500 ? C56 H56 . 0.9500 ?