#------------------------------------------------------------------------------ #$Date: 2015-04-02 13:22:18 +0200 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$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/. 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_2008862 loop_ _publ_author_name 'Fitzgerald, Lawrence J.' 'Gerkin, Roger E.' _publ_section_title ; Hydrogen bonding and C---H···O interactions in bis(8-dimethylamino-1-dimethylammonionaphthalene) [(DMANH^+^)~2~] 4,8-dicarboxynaphthalene-1,5-dicarboxylate dihydrate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1556 _journal_page_last 1559 _journal_paper_doi 10.1107/S0108270199006289 _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 ; _chemical_name_systematic ' ?' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _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_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 14.9 _cell_measurement_theta_min 14.3 _cell_volume 942.9(4) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'TEXSAN and PLATON (Spek, 1990) ' _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device_type AFC5S _diffrn_measurement_method '\w-2theta scans ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.011 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 4566 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% '+- 1.4 (average maximum relative intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method none _exptl_crystal_description 'cut, clear chunk' _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.32 _refine_diff_density_min -0.27 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.86 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 4316 _refine_ls_R_factor_gt 0.038 _refine_ls_shift/su_max 0.0003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/\s^2^~cs~ + (0.002 I)^2^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.067 _reflns_number_gt 3211 _reflns_number_total 4316 _reflns_threshold_expression 'I > 2\sI' _[local]_cod_data_source_file bk1470.cif _[local]_cod_data_source_block I _[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 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_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/\s^2^~cs~ + (0.002 I)^2^' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/\s^2^~cs~ + (0.002 I)^2^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 942.9(3) _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_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson & Simpson (1965)' C 0.003 0.002 'Creagh & McAuley (1992)' O 0.011 0.006 'Creagh & McAuley (1992)' N 0.006 0.003 'Creagh & McAuley (1992)' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 O3 H3 ? ? 120.0(10) yes H11 O5 H12 ? ? 107.0(10) yes C8 N1 C18 ? ? 111.70(10) no C8 N1 C19 ? ? 112.70(10) no C8 N1 H10 ? ? 102.5(8) no C18 N1 C19 ? ? 112.10(10) no C18 N1 H10 ? ? 107.9(8) no C19 N1 H10 ? ? 109.3(8) no C15 N2 C20 ? ? 112.00(10) no C15 N2 C21 ? ? 113.00(10) no C20 N2 C21 ? ? 112.40(10) no C2 C1 C5 ? 2_766 121.40(10) no C2 C1 H1 ? ? 119.7(7) no C5 C1 H1 2_766 ? 118.9(7) no C1 C2 C3 ? ? 119.30(10) no C1 C2 C6 ? ? 115.40(10) no C3 C2 C6 ? ? 125.10(10) yes C2 C3 C3 ? 2_766 119.40(10) no C2 C3 C4 ? ? 122.50(10) yes C3 C3 C4 2_766 ? 118.10(10) no C3 C4 C5 ? ? 120.20(10) no C3 C4 C7 ? ? 122.90(10) yes C5 C4 C7 ? ? 116.00(10) yes C1 C5 C4 2_766 ? 121.20(10) no C1 C5 H2 2_766 ? 118.4(8) no C4 C5 H2 ? ? 120.2(8) no O1 C6 O2 ? ? 124.60(10) yes O1 C6 C2 ? ? 116.80(10) yes O2 C6 C2 ? ? 118.40(10) yes O3 C7 O4 ? ? 120.00(10) yes O3 C7 C4 ? ? 118.40(10) yes O4 C7 C4 ? ? 121.20(10) yes N1 C8 C9 ? ? 118.80(10) no N1 C8 C16 ? ? 119.20(10) yes C9 C8 C16 ? ? 122.00(10) no C8 C9 C10 ? ? 120.10(10) no C8 C9 H4 ? ? 119.9 no C10 C9 H4 ? ? 119.9 no C9 C10 C11 ? ? 120.60(10) no C9 C10 H5 ? ? 119.7 no C11 C10 H5 ? ? 119.7 no C10 C11 C17 ? ? 120.90(10) no C10 C11 H6 ? ? 119.5 no C17 C11 H6 ? ? 119.5 no C13 C12 C17 ? ? 121.10(10) no C13 C12 H7 ? ? 119.5 no C17 C12 H7 ? ? 119.5 no C12 C13 C14 ? ? 120.00(10) no C12 C13 H8 ? ? 120.0 no C14 C13 H8 ? ? 120.0 no C13 C14 C15 ? ? 121.40(10) no C13 C14 H9 ? ? 119.3 no C15 C14 H9 ? ? 119.3 no N2 C15 C14 ? ? 121.40(10) no N2 C15 C16 ? ? 118.40(10) yes C14 C15 C16 ? ? 120.20(10) no C8 C16 C15 ? ? 125.50(10) yes C8 C16 C17 ? ? 116.80(10) no C15 C16 C17 ? ? 117.70(10) no C11 C17 C12 ? ? 120.80(10) yes C11 C17 C16 ? ? 119.60(10) no C12 C17 C16 ? ? 119.60(10) no N1 C18 H18A ? ? 109.5 no N1 C18 H18B ? ? 109.5 no N1 C18 H18C ? ? 109.5 no H18A C18 H18B ? ? 109.5 no H18A C18 H18C ? ? 109.5 no H18B C18 H18C ? ? 109.5 no N1 C19 H19A ? ? 109.5 no N1 C19 H19B ? ? 109.5 no N1 C19 H19C ? ? 109.5 no H19A C19 H19B ? ? 109.5 no H19A C19 H19C ? ? 109.5 no H19B C19 H19C ? ? 109.5 no N2 C20 H20A ? ? 109.5 no N2 C20 H20B ? ? 109.5 no N2 C20 H20C ? ? 109.5 no H20A C20 H20B ? ? 109.5 no H20A C20 H20C ? ? 109.5 no H20B C20 H20C ? ? 109.5 no N2 C21 H21A ? ? 109.5 no N2 C21 H21B ? ? 109.5 no N2 C21 H21C ? ? 109.5 no H21A C21 H21B ? ? 109.5 no H21A C21 H21C ? ? 109.5 no H21B C21 H21C ? ? 109.5 no 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 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O3 H3 O2 2_666 0.99(2) 1.59(2) 2.5770(10) 173(2) yes N1 H10 N2 ? 1.060(10) 1.620(10) 2.620(2) 155.0(10) yes N1 H10 O5 ? 1.060(10) 2.620(10) 3.154(2) 111.0(10) yes O5 H11 O2 2_676 0.86(2) 2.13(2) 2.946(2) 160(2) yes O5 H12 O1 ? 0.92(2) 1.86(2) 2.764(2) 168(2) yes C12 H7 O3 2_565 0.98 2.42 3.331(2) 154 yes C19 H19A O1 1_455 0.98 2.45 3.362(2) 155 yes C9 H4 O4 1_455 0.98 2.49 3.259(2) 135 yes C5 H2 O5 1_545 0.960(10) 2.540(10) 3.390(2) 147.0(10) yes C18 H18B O4 ? 0.98 2.55 3.418(2) 148 yes C21 H21B O5 ? 0.98 2.56 3.229(2) 125 yes C20 H20C O5 ? 0.98 2.59 3.265(2) 127 yes C19 H19C O5 ? 0.98 2.61 3.259(2) 124 yes C18 H18A O2 ? 0.98 2.65 3.342(2) 128 yes C18 H18B O3 ? 0.98 2.66 3.273(2) 121 yes C11 H6 O4 2_565 0.98 2.71 3.671(2) 165 yes C21 H21C O4 ? 0.98 2.78 3.665(2) 150 yes