#------------------------------------------------------------------------------
#$Date: 2008-04-05 09:13:02 +0100 (Sat, 05 Apr 2008) $
#$Revision: 340 $
#$URL: svn://www.crystallography.net/cod/cif/2/2101225.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_2101225
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_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C16 H26 Li2 N2 O15 S2'
_chemical_formula_weight         564.39
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                99.610(10)
_cell_angle_beta                 100.580(10)
_cell_angle_gamma                115.810(10)
_cell_formula_units_Z            2
_cell_length_a                   9.5890(10)
_cell_length_b                   10.4950(10)
_cell_length_c                   14.208(2)
_cell_volume                     1215.2(8)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54178
_exptl_absorpt_coefficient_mu    2.625
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             588
_[local]_cod_data_source_file    gr0362.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
S(1) 1.00315(5) .63309(4) .22359(3)
S(2) .38441(5) .29603(4) .20603(3)
O(1) 1.08610(10) .54690(10) .21063(9)
O(2) 1.1112(2) .78960(10) .27382(9)
O(3) .8952(2) .61280(10) .12786(9)
O(4) .2836(2) .2601(2) .27190(10)
O(5) .3851(2) .16730(10) .14740(10)
O(6) .3500(2) .37820(10) .14030(10)
O(7) 1.2360(2) .8151(2) .63808(9)
O(8) .8934(2) 1.0517(2) .03450(10)
O(9) .6761(2) 1.0054(2) .17820(10)
O(10) 1.0055(2) .9902(2) .23510(10)
O(11) .7061(2) .73440(10) .06290(10)
O(12) 1.0459(2) .66310(10) -.02360(10)
O(13) 1.3370(2) .89050(10) .16220(10)
O(14) 1.3810(2) .8275(2) -.05110(10)
O(15) 1.3848(2) .6275(2) .07660(10)
N(1) 1.1949(2) .7032(2) .43350(10)
N(2) 1.3405(2) .7835(2) .49190(10)
C(1) .8675(2) .5608(2) .29640(10)
C(2) .7092(2) .4700(2) .23930(10)
C(3) .5849(2) .4127(2) .28340(10)
C(4) .6186(2) .4518(2) .38570(10)
C(4A) .7783(2) .5448(2) .44530(10)
C(5) .8078(2) .5887(2) .55200(10)
C(6) .9561(2) .6797(2) .61500(10)
C(7) 1.0948(2) .7322(2) .57860(10)
C(8) 1.0715(2) .6832(2) .47170(10)
C(8A) .9090(2) .5966(2) .40320(10)
C(9) 1.4757(2) .8037(2) .45840(10)
C(10) 1.4612(2) .7376(2) .36090(10)
C(11) 1.6003(2) .7652(2) .33340(10)
C(12) 1.7518(2) .8567(2) .4013(2)
C(13) 1.7648(2) .9203(2) .4984(2)
C(14) 1.6268(2) .8945(2) .52740(10)
Li(1) .8208(4) .9469(3) .1307(2)
Li(2) 1.2767(4) .7350(3) .0380(2)
H(2N) 1.349(3) .826(2) .554(2)
H(2) .679(3) .446(2) .168(2)
H(4) .536(3) .420(2) .415(2)
H(5) .716(3) .555(2) .578(2)
H(6) .973(3) .706(3) .687(2)
H(8W) .926(4) 1.024(4) .009(2)
H(8A) .917(3) 1.140(3) .036(2)
H(9W) .589(3) .957(3) .175(2)
H(9A) .718(3) 1.061(3) .234(2)
H(10W) 1.075(3) 1.062(3) .249(2)
H(10) 1.362(3) .681(3) .317(2)
H(10A) 1.034(3) .926(3) .243(2)
H(11W) .763(3) .697(3) .088(2)
H(11) 1.592(3) .715(3) .268(2)
H(11A) .690(3) .706(3) .000(2)
H(12) 1.843(3) .869(3) .380(2)
H(12W) .985(3) .635(3) .008(2)
H(12A) .993(3) .596(3) -.080(2)
H(13) 1.869(3) .979(3) .547(2)
H(13W) 1.288(3) .867(3) .204(2)
H(13A) 1.333(3) .966(3) .163(2)
H(14) 1.636(3) .940(3) .596(2)
H(14W) 1.350(3) .872(3) -.084(2)
H(14A) 1.453(3) .822(3) -.074(2)
H(15W) 1.365(3) .560(3) .100(2)
H(15A) 1.481(3) .652(3) .071(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S(1) O(1) 1.4520(10)
S(1) O(2) 1.4610(10)
S(1) O(3) 1.4700(10)
S(1) C(1) 1.798(2)
S(2) O(4) 1.4430(10)
S(2) O(5) 1.4680(10)
S(2) O(6) 1.4590(10)
S(2) C(3) 1.769(2)
O(7) C(7) 1.270(2)
N(1) N(2) 1.290(2)
N(1) C(8) 1.341(2)
N(2) C(9) 1.405(2)
C(1) C(2) 1.379(2)
C(1) C(8A) 1.435(2)
C(2) C(3) 1.397(3)
C(3) C(4) 1.377(2)
C(4) C(4A) 1.401(2)
C(4A) C(5) 1.444(2)
C(4A) C(8A) 1.420(2)
C(5) C(6) 1.342(3)
C(6) C(7) 1.431(3)
C(7) C(8) 1.461(2)
C(8) C(8A) 1.455(2)
Li(1) O(8) 1.935(4)
Li(1) O(9) 1.925(4)
Li(1) O(10) 1.911(4)
Li(1) O(11) 1.968(4)
Li(2) O(12) 1.962(4)
Li(2) O(13) 1.989(3)
Li(2) O(14) 1.890(4)
Li(2) O(15) 1.915(4)
O(8) H(8W) .63(3)
O(8) H(8A) .85(3)
O(9) H(9W) .75(3)
O(9) H(9A) .81(3)
O(10) H(10W) .72(3)
O(10) H(10A) .85(3)
O(11) H(11W) .86(3)
O(11) H(11A) .85(3)
O(12) H(12W) .79(3)
O(12) H(12A) .86(3)
O(13) H(13W) .83(3)
O(13) H(13A) .81(3)
O(14) H(14W) .81(3)
O(14) H(14A) .83(3)
O(15) H(15W) .79(3)
O(15) H(15A) .86(3)
N(2) H(2N) .89(2)
C(2) H(2) .96(2)
C(4) H(4) .93(2)
C(5) H(5) .96(2)
C(6) H(6) .97(2)
C(9) C(10) 1.394(2)
C(9) C(14) 1.390(2)
C(10) C(11) 1.381(3)
C(10) H(10) .91(2)
C(11) C(12) 1.388(3)
C(11) H(11) .96(2)
C(12) C(13) 1.386(3)
C(12) H(12) .94(3)
C(13) C(14) 1.386(3)
C(13) H(13) .96(3)
C(14) H(14) .99(2)
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) 114.05(8)
O(1) S(1) O(3) 110.93(7)
O(1) S(1) C(1) 109.01(7)
O(2) S(1) O(3) 110.82(7)
O(2) S(1) C(1) 107.76(7)
O(3) S(1) C(1) 103.68(7)
O(4) S(2) O(5) 113.17(8)
O(4) S(2) O(6) 114.55(9)
O(4) S(2) C(3) 106.32(8)
O(5) S(2) O(6) 109.81(8)
O(5) S(2) C(3) 106.09(8)
O(6) S(2) C(3) 106.25(8)
N(2) N(1) C(8) 118.40(10)
N(1) N(2) C(9) 121.60(10)
S(1) C(1) C(2) 113.10(10)
S(1) C(1) C(8A) 126.20(10)
C(2) C(1) C(8A) 120.5(2)
C(1) C(2) C(3) 121.20(10)
S(2) C(3) C(2) 119.00(10)
S(2) C(3) C(4) 121.00(10)
C(2) C(3) C(4) 119.9(2)
C(3) C(4) C(4A) 120.0(2)
C(4) C(4A) C(5) 118.3(2)
C(4) C(4A) C(8A) 121.60(10)
C(5) C(4A) C(8A) 120.1(2)
C(4A) C(5) C(6) 122.6(2)
C(5) C(6) C(7) 120.6(2)
O(7) C(7) C(6) 120.9(2)
O(7) C(7) C(8) 120.4(2)
C(6) C(7) C(8) 118.6(2)
N(1) C(8) C(7) 122.5(2)
N(1) C(8) C(8A) 117.00(10)
C(7) C(8) C(8A) 120.2(2)
C(1) C(8A) C(4A) 116.5(2)
C(1) C(8A) C(8) 126.1(2)
C(4A) C(8A) C(8) 117.30(10)
N(2) C(9) C(10) 122.4(2)
N(2) C(9) C(14) 116.6(2)
O(8) Li(1) O(9) 108.1(2)
O(8) Li(1) O(10) 108.8(2)
O(8) Li(1) O(11) 108.1(2)
O(9) Li(1) O(10) 112.7(2)
O(9) Li(1) O(11) 110.2(2)
O(10) Li(1) O(11) 108.8(2)
O(12) Li(2) O(13) 105.2(2)
O(12) Li(2) O(14) 104.8(2)
O(12) Li(2) O(15) 129.3(2)
O(13) Li(2) O(14) 107.9(2)
O(13) Li(2) O(15) 104.2(2)
O(14) Li(2) O(15) 104.2(2)
C(10) C(9) C(14) 121.0(2)
C(9) C(10) C(11) 118.7(2)
C(10) C(11) C(12) 120.9(2)
C(11) C(12) C(13) 119.9(2)
C(12) C(13) C(14) 120.1(2)
C(9) C(14) C(13) 119.4(2)