#------------------------------------------------------------------------------ #$Date: 2011-09-28 16:24:46 +0200 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008862.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_2008862 loop_ _publ_author_name 'Fitzgerald, Lawrence J.' 'Gerkin, Roger E.' _publ_section_title ; Hydrogen bonding and C-H...O interactions in (8-dimethylamino-1- dimethylammonionaphthalene^+^)~2~ [(DMANH^+^)~2~] naphthalene-1,5- dicarboxylic acid-4,8-dicarboxylate^-2^ dihydrate ; _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1556 _journal_page_last 1559 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac '2C14 H19 N2 + , C14 H6 O8 2- , 2H2 O' _chemical_formula_moiety 'C14 H19 N2 . C7 H3 O4 . H2 O' _chemical_formula_sum 'C21 H24 N2 O5' _chemical_formula_weight 768.86 _chemical_name_common ; di[1-dimethylamino-8-dimethylammonionaphthalene][naphthalene-1,5-dicarboxylic acid-4,8-dicarboxylate] dihydrate ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 99.000(10) _cell_angle_beta 106.57(2) _cell_angle_gamma 91.54(2) _cell_formula_units_Z 1 _cell_length_a 7.726(2) _cell_length_b 9.818(2) _cell_length_c 13.169(2) _cell_measurement_temperature 296 _cell_volume 942.9(3) _diffrn_ambient_temperature 296 _exptl_crystal_density_diffrn 1.354 _[local]_cod_chemical_formula_sum_orig 'C21 H24 N2 O5 ' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value 28 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana ; _cod_database_code 2008862 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -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_calc_attached_atom O1 0.74570(10) 0.86320(10) 0.43886(8) 0.0439(3) Uani ? ? O2 0.61300(10) 0.71539(10) 0.50998(8) 0.0352(3) Uani ? ? O3 0.42990(10) 0.44200(10) 0.35837(8) 0.0376(3) Uani ? ? O4 0.59590(10) 0.56040(10) 0.28701(7) 0.0385(3) Uani ? ? O5 0.4622(2) 1.02490(10) 0.37015(9) 0.0467(3) Uani ? ? N1 0.12470(10) 0.81610(10) 0.24346(8) 0.0269(3) Uani ? ? N2 0.30950(10) 0.89960(10) 0.12297(9) 0.0304(3) Uani ? ? C1 1.0716(2) 0.75880(10) 0.54550(10) 0.0281(4) Uani ? ? C2 0.9123(2) 0.67840(10) 0.49870(10) 0.0244(3) Uani ? ? C3 0.9157(2) 0.53080(10) 0.48035(9) 0.0225(3) Uani ? ? C4 0.7573(2) 0.44030(10) 0.42288(10) 0.0244(3) Uani ? ? C5 0.7647(2) 0.30000(10) 0.41460(10) 0.0275(4) Uani ? ? C6 0.7420(2) 0.75650(10) 0.47860(10) 0.0281(4) Uani ? ? C7 0.5888(2) 0.48930(10) 0.35340(10) 0.0277(4) Uani ? ? C8 0.0005(2) 0.73520(10) 0.14450(10) 0.0269(3) Uani ? ? C9 -0.1427(2) 0.6577(2) 0.15200(10) 0.0378(4) Uani ? ? C10 -0.2626(2) 0.5788(2) 0.05940(10) 0.0453(5) Uani ? ? C11 -0.2383(2) 0.5794(2) -0.03830(10) 0.0432(4) Uani ? ? C12 -0.0610(2) 0.6540(2) -0.15060(10) 0.0464(5) Uani ? ? C13 0.0832(3) 0.7256(2) -0.16120(10) 0.0551(5) Uani ? ? C14 0.2065(2) 0.8057(2) -0.07040(10) 0.0481(5) Uani ? ? C15 0.1845(2) 0.81370(10) 0.02960(10) 0.0315(4) Uani ? ? C16 0.0358(2) 0.73780(10) 0.04420(10) 0.0271(3) Uani ? ? C17 -0.0892(2) 0.65700(10) -0.04920(10) 0.0345(4) Uani ? ? C18 0.2249(2) 0.7247(2) 0.31760(10) 0.0390(4) Uani ? ? C19 0.0333(2) 0.9230(2) 0.29860(10) 0.0417(4) Uani ? ? C20 0.3020(2) 1.0474(2) 0.11610(10) 0.0505(5) Uani ? ? C21 0.4953(2) 0.8559(2) 0.14640(10) 0.0502(5) Uani ? ? H1 1.071(2) 0.8600(10) 0.5540(10) 0.032(4) Uiso ? ? H2 0.659(2) 0.2390(10) 0.3758(10) 0.030(4) Uiso ? ? H3 0.424(2) 0.384(2) 0.412(2) 0.102(7) Uiso ? ? H4 -0.1621 0.6570 0.2223 0.0454 Uiso calc C9 H5 -0.3650 0.5228 0.0654 0.0544 Uiso calc C10 H6 -0.3249 0.5255 -0.1024 0.0518 Uiso calc C11 H7 -0.1471 0.5992 -0.2146 0.0557 Uiso calc C12 H8 0.1015 0.7215 -0.2322 0.0661 Uiso calc C13 H9 0.3107 0.8568 -0.0790 0.0577 Uiso calc C14 H10 0.219(2) 0.865(2) 0.2140(10) 0.057(5) Uiso ? ? H11 0.449(2) 1.090(2) 0.419(2) 0.082(7) Uiso ? ? H12 0.556(2) 0.976(2) 0.4030(10) 0.070(6) Uiso ? ? H18A 0.3073 0.7818 0.3819 0.0469 Uiso calc C18 H18B 0.2948 0.6636 0.2809 0.0469 Uiso calc C18 H18C 0.1383 0.6688 0.3387 0.0469 Uiso calc C18 H19A -0.0575 0.8776 0.3237 0.0501 Uiso calc C19 H19B -0.0261 0.9829 0.2482 0.0501 Uiso calc C19 H19C 0.1233 0.9787 0.3602 0.0501 Uiso calc C19 H20A 0.1762 1.0718 0.1011 0.0606 Uiso calc C20 H20B 0.3501 1.0665 0.0580 0.0606 Uiso calc C20 H20C 0.3749 1.1023 0.1844 0.0606 Uiso calc C20 H21A 0.5432 0.8658 0.0863 0.0603 Uiso calc C21 H21B 0.5718 0.9137 0.2123 0.0603 Uiso calc C21 H21C 0.4947 0.7589 0.1560 0.0603 Uiso calc C21 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 0.0380(6) 0.0375(6) 0.0658(7) 0.0147(5) 0.0209(5) 0.0254(6) O2 0.0279(5) 0.0408(6) 0.0440(6) 0.0092(4) 0.0182(5) 0.0133(5) O3 0.0198(5) 0.0477(6) 0.0451(6) 0.0011(4) 0.0032(4) 0.0194(5) O4 0.0362(6) 0.0491(6) 0.0335(5) 0.0057(5) 0.0088(4) 0.0185(5) O5 0.0442(7) 0.0442(7) 0.0450(7) 0.0128(6) 0.0055(6) 0.0010(6) N1 0.0250(6) 0.0317(6) 0.0243(6) 0.0032(5) 0.0081(5) 0.0044(5) N2 0.0268(6) 0.0320(6) 0.0336(6) 0.0013(5) 0.0103(5) 0.0071(5) C1 0.0297(7) 0.0256(7) 0.0311(7) 0.0048(6) 0.0123(6) 0.0047(6) C2 0.0242(7) 0.0284(7) 0.0236(7) 0.0065(6) 0.0105(5) 0.0061(5) C3 0.0213(6) 0.0272(7) 0.0215(6) 0.0047(5) 0.0093(5) 0.0054(5) C4 0.0214(6) 0.0307(7) 0.0229(7) 0.0037(5) 0.0088(5) 0.0059(5) C5 0.0236(7) 0.0303(7) 0.0274(7) -0.0011(6) 0.0070(6) 0.0028(6) C6 0.0262(7) 0.0292(7) 0.0290(7) 0.0065(6) 0.0086(6) 0.0037(6) C7 0.0241(7) 0.0306(7) 0.0267(7) 0.0035(6) 0.0052(6) 0.0033(6) C8 0.0226(7) 0.0281(7) 0.0286(7) 0.0052(6) 0.0054(5) 0.0045(6) C9 0.0285(8) 0.0439(9) 0.0424(9) 0.0019(7) 0.0119(7) 0.0092(7) C10 0.0264(8) 0.0432(9) 0.0610(10) -0.0051(7) 0.0068(7) 0.0056(8) C11 0.0290(8) 0.0377(9) 0.0493(10) 0.0021(7) -0.0043(7) -0.0030(7) C12 0.0570(10) 0.0433(10) 0.0301(8) 0.0103(8) 0.0017(8) -0.0012(7) C13 0.0770(10) 0.0630(10) 0.0271(8) 0.0090(10) 0.0187(8) 0.0058(8) C14 0.0570(10) 0.0570(10) 0.0369(9) -0.0011(9) 0.0222(8) 0.0105(8) C15 0.0341(8) 0.0328(8) 0.0287(7) 0.0057(6) 0.0101(6) 0.0060(6) C16 0.0264(7) 0.0262(7) 0.0278(7) 0.0077(6) 0.0052(6) 0.0058(6) C17 0.0346(8) 0.0313(8) 0.0313(8) 0.0097(6) 0.0009(6) 0.0021(6) C18 0.0374(8) 0.0469(9) 0.0324(8) 0.0056(7) 0.0043(6) 0.0159(7) C19 0.0385(9) 0.0434(9) 0.0439(9) 0.0081(7) 0.0185(7) -0.0034(7) C20 0.0620(10) 0.0358(9) 0.0530(10) -0.0025(8) 0.0128(9) 0.0121(8) C21 0.0327(8) 0.0720(10) 0.0496(10) 0.0123(8) 0.0152(7) 0.0125(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 ? ? 1.245(2) yes O2 C6 ? ? 1.262(2) yes O3 C7 ? ? 1.324(2) yes O3 H3 ? ? 0.99(2) no O4 C7 ? ? 1.212(2) yes O5 H11 ? ? 0.86(2) no O5 H12 ? ? 0.92(2) no N1 C8 ? ? 1.474(2) no N1 C18 ? ? 1.496(2) no N1 C19 ? ? 1.491(2) no N1 H10 ? ? 1.060(10) no N2 C15 ? ? 1.453(2) no N2 C20 ? ? 1.469(2) no N2 C21 ? ? 1.471(2) no C1 C2 ? ? 1.372(2) no C1 C5 ? 2_766 1.402(2) no C1 H1 ? ? 0.980(10) no C2 C3 ? ? 1.434(2) no C2 C6 ? ? 1.519(2) no C3 C3 ? 2_766 1.444(2) no C3 C4 ? ? 1.436(2) no C4 C5 ? ? 1.368(2) no C4 C7 ? ? 1.503(2) no C5 H2 ? ? 0.960(10) no C8 C9 ? ? 1.362(2) no C8 C16 ? ? 1.426(2) no C9 C10 ? ? 1.403(2) no C9 H4 ? ? 0.980 no C10 C11 ? ? 1.352(2) no C10 H5 ? ? 0.980 no C11 C17 ? ? 1.417(2) no C11 H6 ? ? 0.980 no C12 C13 ? ? 1.353(2) no C12 C17 ? ? 1.410(2) no C12 H7 ? ? 0.980 no C13 C14 ? ? 1.404(2) no C13 H8 ? ? 0.980 no C14 C15 ? ? 1.366(2) no C14 H9 ? ? 0.980 no C15 C16 ? ? 1.428(2) no C16 C17 ? ? 1.433(2) no C18 H18A ? ? 0.980 no C18 H18B ? ? 0.980 no C18 H18C ? ? 0.980 no C19 H19A ? ? 0.980 no C19 H19B ? ? 0.980 no C19 H19C ? ? 0.980 no C20 H20A ? ? 0.980 no C20 H20B ? ? 0.980 no C20 H20C ? ? 0.980 no C21 H21A ? ? 0.980 no C21 H21B ? ? 0.980 no C21 H21C ? ? 0.980 no