#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/13/2101390.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_2101390
loop_
_publ_author_name
'Nagata, H.'
'In, Y.'
'Doi, M.'
'Ishida, T.'
'Wakahara, A.'
_publ_section_title
;
 Structural features of four tryptophan metabolite--picric acid
 molecular complexes
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1051
_journal_page_last               1058
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C16 H12 N4 O9'
_chemical_formula_weight         404.300
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                93.78(6)
_cell_angle_beta                 99.96(7)
_cell_angle_gamma                100.19(3)
_cell_formula_units_Z            2
_cell_length_a                   7.628(5)
_cell_length_b                   16.715(6)
_cell_length_c                   6.850(2)
_cell_volume                     842.5(7)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    1.075
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      1.576(3)
_exptl_crystal_F_000             416
_[local]_cod_data_source_file    as0686.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C(1) .3231(7) .8560(3) .8394(7) .056(3)
O(1) .4344(7) .9282(3) .8760(7) .066(3)
C(2) .3722(6) .7807(3) .8672(7) .052(3)
N(2) .5628(6) .7773(4) .9495(8) .074(3)
O(2) .6756(6) .8380(3) .9565(9) .114(4)
O(2') .5945(6) .7134(3) 1.0080(8) .110(4)
C(3) .2532(7) .7074(3) .830(7) .052(3)
C(4) .0739(6) .7088(3) .7563(7) .049(3)
N(4) -.0568(7) .6298(3) .7148(7) .067(3)
O(4) .0042(7) .5682(3) .7054(8) .101(4)
O(4') -.2160(6) .6326(3) .6918(9) .115(4)
C(5) .0121(7) .7795(3) .7228(7) .054(3)
C(6) .1338(8) .8517(3) .7652(7) .059(3)
N(6) .0660(10) .9275(4) .7361(9) .093(4)
O(6) -0.0873(8) .9216(3) .6450(10) .135(5)
O(6') .1650(10) .9915(3) .7980(10) .152(6)
O(1') -.147(2) .7800(10) .646(2) .090(10)
N(1A) -.0196(5) .7057(3) .2223(6) .057(3)
C(2A) .0464(7) .6357(3) .2496(8) .056(3)
C(3A) .2296(6) .6550(3) .3190(7) .049(3)
C(4A) .4460(7) .7978(3) .3878(7) .054(3)
C(5A) .4444(8) .8789(4) .3774(9) .069(4)
C(6A) .2830(10) .9075(3) .3152(9) .075(4)
C(7A) .1208(8) .8543(3) .2601(8) .063(4)
C(8A) .1206(6) .7720(3) .2671(7) .049(3)
C(9A) .2792(6) .7405(3) .3314(7) .045(3)
C(10A) .3549(7) .5962(3) .3782(8) .057(3)
C(11A) .4190(7) .5566(3) .2083(8) .056(3)
O(12A) .3254(5) .5403(2) .0411(6) .073(3)
O(12'A) .5758(3) .5361(3) .2550(6) .082(3)
H(3) .2984 .6500 .8552 .050
H(1A) -.1413 .7057 .1403 .050
H(2A) -.0340 .5747 .2213 .050
H(4A) .5507 .7662 .4403 .050
H(5A) .5707 .9113 .4272 .050
H(6A) .2893 .9735 .3109 .050
H(7A) -.0066 .8759 .2117 .050
H(10a) .4771 .6388 .4484 .050
H(10b) .2588 .5454 .4117 .050
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1) O(1) 1.328(7)
C(1) C(2) 1.390(7)
C(1) C(6) 1.433(7)
C(2) N(2) 1.478(8)
C(2) C(3) 1.371(7)
N(2) O(2) 1.202(8)
N(2) O(2') 1.213(7)
C(3) C(4) 1.379(7)
C(4) N(4) 1.485(7)
C(4) C(5) 1.367(7)
N(4) O(4) 1.204(7)
N(4) O(4') 1.208(7)
C(5) C(6) 1.366(7)
C(5) O(1') 1.24(2)
C(6) N(6) 1.463(8)
N(6) O(6) 1.212(9)
N(6) O(6') 1.201(9)
N(1A) C(2A) 1.365(7)
N(1A) C(8A) 1.374(6)
C(2A) C(3A) 1.369(7)
C(3A) C(9A) 1.405(6)
C(3A) C(10A) 1.515(7)
C(4A) C(5A) 1.365(8)
C(4A) C(9A) 1.427(7)
C(5A) C(6A) 1.405(9)
C(6A) C(7A) 1.368(8)
C(7A) C(8A) 1.380(7)
C(8A) C(9A) 1.417(6)
C(10A) C(11A) 1.497(7)
C(11A) O(12A) 1.226(6)
C(11A) O(12'A) 1.296(7)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O(1) C(1) C(2) 125.8(3)
O(1) C(1) C(6) 119.7(3)
C(2) C(1) C(6) 114.4(3)
C(1) C(2) N(2) 119.6(3)
C(1) C(2) C(3) 124.3(3)
N(2) C(2) C(3) 116.0(3)
C(2) N(2) O(2) 117.9(3)
C(2) N(2) O(2') 117.7(3)
O(2) N(2) O(2') 124.3(4)
C(2) C(3) C(4) 117.4(3)
C(3) C(4) N(4) 118.1(3)
C(3) C(4) C(5) 122.8(3)
N(4) C(4) C(5) 119.2(3)
C(4) N(4) O(4) 117.6(3)
C(4) N(4) O(4') 117.1(3)
O(4) N(4) O(4') 125.3(4)
C(4) C(5) C(6) 118.3(3)
C(4) C(5) O(1') 122.4(7)
C(6) C(5) O(1') 119.2(7)
C(1) C(6) C(5) 122.8(3)
C(1) C(6) N(6) 119.1(3)
C(5) C(6) N(6) 118.1(4)
C(6) N(6) O(6) 117.3(4)
C(6) N(6) O(6') 118.9(4)
O(6) N(6) O(6') 123.7(5)
C(2A) N(1A) C(8A) 109.6(3)
N(1A) C(2A) C(3A) 109.4(3)
C(2A) C(3A) C(9A) 106.8(3)
C(2A) C(3A) C(10A) 126.9(3)
C(9A) C(3A) C(10A) 126.2(3)
C(5A) C(4A) C(9A) 118.8(3)
C(4A) C(5A) C(6A) 121.9(4)
C(5A) C(6A) C(7A) 120.9(4)
C(6A) C(7A) C(8A) 117.9(3)
N(1A) C(8A) C(7A) 130.6(3)
N(1A) C(8A) C(9A) 106.1(3)
C(7A) C(8A) C(9A) 123.2(3)
C(3A) C(9A) C(4A) 134.8(3)
C(3A) C(9A) C(8A) 107.9(3)
C(4A) C(9A) C(8A) 117.3(3)
C(3A) C(10A) C(11A) 114.6(3)
C(10A) C(11A) O(12A) 122.5(3)
C(10A) C(11A) O(12'A) 114.7(3)
O(12A) C(11A) O(12'A) 122.6(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O(1) C(1) C(2) N(2) 1.7(5)
O(1) C(1) C(2) C(3) 179.2(6)
C(6) C(1) C(2) N(2) -178.0(5)
C(6) C(1) C(2) C(3) -0.6(5)
O(1) C(1) C(6) C(5) 179.4(6)
O(1) C(1) C(6) N(6) -1.6(5)
C(2) C(1) C(6) C(5) -0.8(5)
C(2) C(1) C(6) N(6) 178.2(6)
C(1) C(2) N(2) O(2) -13.2(5)
C(1) C(2) N(2) O(2') 165.9(6)
C(3) C(2) N(2) O(2) 169.2(6)
C(3) C(2) N(2) O(2') -11.8(5)
C(1) C(2) C(3) C(4) 1.4(4)
N(2) C(2) C(3) C(4) 179.0(5)
C(2) C(3) C(4) N(4) 179.8(5)
C(2) C(3) C(4) C(5) -1.0(5)
C(3) C(4) N(4) O(4) -15.9(5)
C(3) C(4) N(4) O(4') 164.6(6)
C(5) C(4) N(4) O(4) 164.9(6)
C(5) C(4) N(4) O(4') 14.6(5)
C(3) C(4) C(5) C(6) -0.2(5)
C(3) C(4) C(5) O(1') 176.0(10)
N(4) C(4) C(5) C(6) 178.9(6)
N(4) C(4) C(5) O(1') -5.0(10)
C(4) C(5) C(6) C(1) 1.2(5)
C(4) C(5) C(6) N(6) -177.8(6)
O(1') C(5) C(6) C(1) -175.0(10)
O(1') C(5) C(6) N(6) 6.0(10)
C(1) C(6) N(6) O(6) 168.7(7)
C(1) C(6) N(6) O(6') -9.3(6)
C(5) C(6) N(6) O(6) -12.3(6)
C(5) C(6) N(6) O(6') 169.7(8)
C(8A) N(1A) C(2A) C(3A) 2.0(4)
C(2A) N(1A) C(8A) C(7A) 179.3(6)
C(2A) N(1A) C(8A) C(9A) -2.0(4)
N(1A) C(2A) C(3A) C(9A) -1.1(4)
N(1A) C(2A) C(3A) C(10A) 177.0(5)
C(2A) C(3A) C(9A) C(4A) -178.6(6)
C(2A) C(3A) C(9A) C(8A) -0.1(4)
C(10A) C(3A) C(9A) C(4A) 3.3(6)
C(10A) C(3A) C(9A) C(8A) -178.2(5)
C(2A) C(3A) C(10A) C(11A) 83.3(5)
C(9A) C(3A) C(10A) C(11A) -98.9(5)
C(9A) C(4A) C(5A) C(6A) 0.8(5)
C(5A) C(4A) C(9A) C(3A) 178.5(7)
C(5A) C(4A) C(9A) C(8A) 0.1(5)
C(4A) C(5A) C(6A) C(7A) -0.8(6)
C(5A) C(6A) C(7A) C(8A) -0.2(5)
C(6A) C(7A) C(8A) N(1A) 179.6(6)
C(6A) C(7A) C(8A) C(9A) 1.1(5)
N(1A) C(8A) C(9A) C(3A) 1.3(4)
N(1A) C(8A) C(9A) C(4A) -179.9(5)
C(7A) C(8A) C(9A) C(3A) -179.9(5)
C(7A) C(8A) C(9A) C(4A) -1.1(4)
C(3A) C(10A) C(11A) O(12A) -32.6(5)
C(3A) C(10A) C(11A) O(12'A) 151.8(5)
_cod_database_code 2101390