#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/12/2101224.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_2101224 loop_ _publ_author_name 'Ojala, W. H.' 'Lu, L. K.' 'Albers, K. E.' 'Gleason, W. B.' 'Richardson, T. I.' 'Lovrien, R. E.' 'Sudbeck, E. A.' _publ_section_title ; Intermolecular interactions of sulfonated azo dyes: crystal structures of the diammonium, dilithium, magnesium and calcium salts of 7-hydroxy-8-(phenylazo)-1,3-naphthalenedisulfonic acid(Orange G) ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 684 _journal_page_last 694 _journal_paper_doi 10.1107/S0108768194005203 _journal_volume 50 _journal_year 1994 _chemical_formula_sum 'C16 H26 N4 O11 S2' _chemical_formula_weight 514.52 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _cell_angle_alpha 87.43(2) _cell_angle_beta 88.070(10) _cell_angle_gamma 71.00(2) _cell_formula_units_Z 2 _cell_length_a 9.1650(10) _cell_length_b 10.149(4) _cell_length_c 12.6230(10) _cell_volume 1108.8(5) _diffrn_radiation_type Cu _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 2.724 _exptl_crystal_density_diffrn 1.541 _exptl_crystal_F_000 540 _cod_data_source_file gr0362.cif _cod_data_source_block gr0362a _cod_original_cell_volume 1108.8(8) _cod_database_code 2101224 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,-y,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z S(1) .38722(6) .76055(6) .28882(4) S(2) .95406(6) .38658(6) .31091(4) O(1) .2731(2) .6902(2) .31070(10) O(2) .3274(2) .8913(2) .22600(10) O(3) .4594(2) .7805(2) .38540(10) O(4) 1.0794(2) .3117(2) .24140(10) O(5) .8916(2) .2916(2) .37510(10) O(6) .9931(2) .4822(2) .3780(2) O(7) .3559(2) .7683(2) -.15300(10) O(8) .3525(2) 1.1223(2) .32920(10) O(9) .6639(2) .9162(2) .45370(10) O(10) 1.0263(3) .0022(3) .3278(3) O(11) .3281(2) .4324(2) .4233(2) N(1) .2841(2) .7352(2) .06610(10) N(2) .1702(2) .7912(2) .00220(10) N(3) .6116(2) .2143(3) .3783(2) N(4) 1.0248(3) .2388(3) .5782(2) C(1) .5422(2) .6454(2) .2130(2) C(2) .6646(3) .5678(2) .2754(2) C(3) .8021(2) .4863(2) .2289(2) C(4) .8214(3) .4872(2) .1201(2) C(4A) .6996(3) .5632(2) .0558(2) C(5) .7258(3) .5648(3) -.0573(2) C(6) .6159(3) .6347(3) -.1254(2) C(7) .4605(3) .7076(2) -.0877(2) C(8) .4284(3) .7016(2) .0260(2) C(8A) .5530(3) .6378(2) .1002(2) C(9) .0155(3) .8206(2) .0376(2) C(10) -.0225(3) .7946(3) .1418(2) C(11) -.1777(3) .8315(3) .1717(2) C(12) -.2924(3) .8928(3) .0982(2) C(13) -.2520(3) .9137(3) -.0061(2) C(14) -.0971(3) .8781(3) -.0370(2) H(2) .653(3) .572(3) .349(3) H(2N) .188(4) .803(3) -.058(3) H(3A) .525(4) .277(4) .401(3) H(3B) .629(4) .128(4) .402(3) H(3C) .689(4) .246(4) .397(3) H(3D) .612(4) .212(4) .306(3) H(4) .919(4) .433(3) .081(2) H(4A) .972(4) .278(4) .513(3) H(4B) .983(5) .182(5) .610(3) H(4C) 1.132(5) .188(4) .569(3) H(4D) 1.019(5) .320(5) .611(3) H(5) .831(4) .507(4) -.086(2) H(6) .637(4) .637(4) -.204(3) H(8W) .359(4) 1.048(4) .305(3) H(8A) .281(4) 1.173(4) .301(3) H(9W) .618(4) .887(4) .427(3) H(9A) .660(4) .906(4) .532(3) H(10) .058(4) .754(4) .183(3) H(10W) 1.094(6) -.022(6) .303(4) H(10A) .996(5) .091(5) .346(3) H(11W) .318(4) .525(5) .396(3) H(11) -.209(4) .817(4) .249(3) H(11A) .261(5) .431(5) .416(4) H(12) -.405(4) .915(4) .121(3) H(13) -.332(4) .962(4) -.053(3) H(14) -.068(4) .886(4) -.107(3) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O(1) S(1) O(2) 113.50(10) O(1) S(1) O(3) 111.90(10) O(1) S(1) C(1) 107.40(10) O(2) S(1) O(3) 111.50(10) O(2) S(1) C(1) 107.30(10) O(3) S(1) C(1) 104.50(10) O(4) S(2) O(5) 111.90(10) O(4) S(2) O(6) 113.60(10) O(4) S(2) C(3) 106.90(10) O(5) S(2) O(6) 110.70(10) O(5) S(2) C(3) 105.70(10) O(6) S(2) C(3) 107.60(10) N(2) N(1) C(8) 118.2(2) N(1) N(2) C(9) 121.1(2) S(1) C(1) C(2) 112.7(2) S(1) C(1) C(8A) 126.5(2) C(2) C(1) C(8A) 120.5(2) C(1) C(2) C(3) 120.6(2) S(2) C(3) C(2) 119.3(2) S(2) C(3) C(4) 120.5(2) C(2) C(3) C(4) 120.2(2) C(3) C(4) C(4A) 120.1(2) C(4) C(4A) C(5) 118.4(2) C(4) C(4A) C(8A) 121.1(2) C(5) C(4A) C(8A) 120.5(2) C(4A) C(5) C(6) 122.7(2) C(5) C(6) C(7) 120.6(2) O(7) C(7) C(6) 120.2(2) O(7) C(7) C(8) 121.9(2) C(6) C(7) C(8) 117.8(2) N(1) C(8) C(7) 122.1(2) N(1) C(8) C(8A) 116.5(2) C(7) C(8) C(8A) 120.7(2) C(1) C(8A) C(4A) 116.8(2) C(1) C(8A) C(8) 126.3(2) C(4A) C(8A) C(8) 116.9(2) N(2) C(9) C(10) 122.0(2) N(2) C(9) C(14) 116.6(2) C(10) C(9) C(14) 121.4(2) C(9) C(10) C(11) 118.6(2) C(10) C(11) C(12) 120.7(2) C(11) C(12) C(13) 119.8(2) C(12) C(13) C(14) 120.1(2) C(9) C(14) C(13) 119.3(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S(1) O(1) 1.459(2) S(1) O(2) 1.466(2) S(1) O(3) 1.460(2) S(1) C(1) 1.796(2) S(2) O(4) 1.446(2) S(2) O(5) 1.473(2) S(2) O(6) 1.452(2) S(2) C(3) 1.766(2) O(7) C(7) 1.265(3) N(1) N(2) 1.301(3) N(1) C(8) 1.341(3) N(2) C(9) 1.412(3) C(1) C(2) 1.388(3) C(1) C(8A) 1.428(3) C(2) C(3) 1.390(3) C(3) C(4) 1.379(3) C(4) C(4A) 1.394(3) C(4A) C(5) 1.440(3) C(4A) C(8A) 1.421(3) C(5) C(6) 1.340(3) C(6) C(7) 1.450(3) C(7) C(8) 1.459(3) C(8) C(8A) 1.461(3) O(8) H(8W) .81(4) O(8) H(8A) .77(4) O(9) H(9W) .69(4) O(9) H(9A) .98(4) O(10) H(10W) .66(5) O(10) H(10A) .89(5) O(11) H(11W) .96(5) O(11) H(11A) .63(4) N(2) H(2N) .78(3) N(3) H(3A) .89(4) N(3) H(3B) .88(4) N(3) H(3C) .90(3) N(3) H(3D) .91(4) N(4) H(4A) .97(4) N(4) H(4B) .87(5) N(4) H(4C) .95(4) N(4) H(4D) .92(4) C(2) H(2) .93(3) C(4) H(4) 1.01(3) C(5) H(5) 1.01(3) C(6) H(6) 1.00(3) C(9) C(10) 1.385(3) C(9) C(14) 1.384(3) C(10) C(11) 1.392(3) C(10) H(10) .89(4) C(11) C(12) 1.392(4) C(11) H(11) 1.03(4) C(12) C(13) 1.392(4) C(12) H(12) 1.01(3) C(13) C(14) 1.393(3) C(13) H(13) .95(3) C(14) H(14) .93(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063209