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#$Date: 2022-09-28 18:08:17 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/13/2101388.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_2101388
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_paper_doi               10.1107/S0108768195005349
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C16 H13 N5 O8'
_chemical_formula_weight         403.315
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                91.10(3)
_cell_angle_beta                 106.76(3)
_cell_angle_gamma                77.24(4)
_cell_formula_units_Z            2
_cell_length_a                   8.027(3)
_cell_length_b                   15.900(8)
_cell_length_c                   7.176(2)
_cell_volume                     854.3(6)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    0.997
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      1.547(3)
_exptl_crystal_F_000             416
_cod_data_source_file            as0686.cif
_cod_data_source_block           as0686a
_cod_original_cell_volume        854.4(6)
_cod_database_code               2101388
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
_atom_site_U_iso_or_equiv
C(1) .3238(4) .2201(2) .3542(4) .046(2)
O(1) .3289(3) .1439(2) .2796(4) .0630(10)
C(2) .1742(4) .2887(2) .3317(4) .048(2)
N(2) -.0042(4) .2788(2) .2261(4) .057(2)
O(2) -.0259(4) .2060(2) .1933(5) .089(2)
O(2') -.1232(4) .3426(2) .1740(6) .087(2)
C(3) .1869(4) .3680(2) .4098(4) .047(2)
C(4) .3509(4) .3799(2) .5146(4) .050(2)
N(4) .3649(4) .4637(2) .5965(4) .064(2)
O(4) .2328(5) .5219(2) .5546(5) .088(2)
O(4') .5104(4) .4708(2) .7024(4) .083(2)
C(5) .5036(4) .3154(2) .5434(4) .050(2)
C(6) .4868(4) .2376(2) .4643(4) .046(2)
N(6) .6522(4) .1713(2) .4934(5) .065(2)
O(6) .7870(4) .1945(3) .4925(7) .113(3)
O(6') .6513(5) .0963(2) .5118(6) .099(3)
N(1A) .5714(4) .2096(2) .9849(5) .064(2)
C(2A) .5236(5) .1368(2) .9039(5) .059(2)
C(3A) .3432(4) .1520(2) .8257(4) .047(2)
C(4A) .1035(4) .2936(2) .8087(5) .054(2)
C(5A) .0865(6) .3789(3) .8598(6) .072(2)
C(6A) .2366(7) .4102(2) .9614(6) .082(3)
C(7A) .4041(6) .3596(3) 1.0117(5) .073(2)
C(8A) .4214(4) .2743(3) .9574(4) .054(2)
C(9A) .2747(4) .2397(2) .8576(4) .044(2)
C(10A) .2409(6) .0883(2) .7217(5) .068(2)
C(11A) .1431(4) .0505(2) .8383(4) .050(2)
N(12A) .0797(4) -.0168(2) .7641(4) .060(2)
O(12A) .1219(4) .0791(2) .9908(4) .092(2)
H(1) .226(5) .137(2) .168(5) .112(9)
H(3) .088(5) .410(2) .393(5) .060(9)
H(5) .628(5) .315(2) .623(5) .002(9)
H(1A) .689(5) .214(2) 1.048(5) .090(9)
H(2A) .600(5) .083(2) .894(5) .070(9)
H(4A) .002(5) .272(2) .732(5) .059(9)
H(5A) -.021(5) .417(2) .828(5) .091(9)
H(6A) .214(5) .469(2) .994(5) .083(9)
H(7A) .506(5) .389(2) 1.081(5) .061(9)
H(10a) .306(5) .043(3) .688(5) .076(9)
H(10b) .160(5) .116(2) .589(6) .082(9)
H(12a) .058(5) -.023(2) .617(6) .120(9)
H(12b) .003(5) -.038(2) .831(5) .082(9)
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) 127.7(2)
O(1) C(1) C(6) 117.2(2)
C(2) C(1) C(6) 115.1(2)
C(1) C(2) N(2) 121.0(2)
C(1) C(2) C(3) 122.5(2)
N(2) C(2) C(3) 116.5(2)
C(2) N(2) O(2) 117.9(2)
C(2) N(2) O(2') 119.0(2)
O(2) N(2) O(2') 123.1(2)
C(2) C(3) C(4) 118.8(2)
C(3) C(4) N(4) 119.0(2)
C(3) C(4) C(5) 121.9(2)
N(4) C(4) C(5) 119.1(2)
C(4) N(4) O(4) 118.2(2)
C(4) N(4) O(4') 117.8(2)
O(4) N(4) O(4') 124.0(2)
C(4) C(5) C(6) 117.9(2)
C(1) C(6) C(5) 123.8(2)
C(1) C(6) N(6) 119.7(2)
C(5) C(6) N(6) 116.4(2)
C(6) N(6) O(6) 118.1(2)
C(6) N(6) O(6') 120.0(2)
O(6) N(6) O(6') 121.9(3)
C(2A) N(1A) C(8A) 109.1(2)
N(1A) C(2A) C(3A) 110.1(2)
C(2A) C(3A) C(10A) 125.8(2)
C(2A) C(3A) C(9A) 106.5(2)
C(10A) C(3A) C(9A) 127.7(2)
C(3A) C(10A) C(11A) 114.8(2)
C(10A) C(11A) O(12A) 123.3(2)
C(10A) C(11A) N(12A) 115.6(2)
O(12A) C(11A) N(12A) 121.0(2)
C(5A) C(4A) C(9A) 118.2(2)
C(4A) C(5A) C(6A) 121.0(3)
C(5A) C(6A) C(7A) 122.2(3)
C(6A) C(7A) C(8A) 116.8(3)
N(1A) C(8A) C(7A) 129.8(2)
N(1A) C(8A) C(9A) 107.1(2)
C(7A) C(8A) C(9A) 123.1(2)
C(3A) C(9A) C(4A) 134.0(2)
C(3A) C(9A) C(8A) 107.3(2)
C(4A) C(9A) C(8A) 118.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1) O(1) 1.312(4)
C(1) C(2) 1.405(4)
C(1) C(6) 1.403(4)
C(2) N(2) 1.456(4)
C(2) C(3) 1.383(4)
N(2) O(2) 1.216(4)
N(2) O(2') 1.209(5)
C(3) C(4) 1.367(4)
C(4) N(4) 1.459(4)
C(4) C(5) 1.381(4)
N(4) O(4) 1.211(5)
N(4) O(4') 1.223(4)
C(5) C(6) 1.368(4)
C(6) N(6) 1.465(5)
N(6) O(6) 1.218(6)
N(6) O(6') 1.205(5)
N(1A) C(2A) 1.366(5)
N(1A) C(8A) 1.368(5)
C(2A) C(3A) 1.361(5)
C(3A) C(10A) 1.496(5)
C(3A) C(9A) 1.422(4)
C(4A) C(5A) 1.387(6)
C(4A) C(9A) 1.400(5)
C(5A) C(6A) 1.405(6)
C(6A) C(7A) 1.356(6)
C(7A) C(8A) 1.392(5)
C(8A) C(9A) 1.410(4)
C(10A) C(11A) 1.511(5)
C(11A) O(12A) 1.220(4)
C(11A) N(12A) 1.322(4)
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) 4.4(3)
O(1) C(1) C(2) C(3) -176.6(4)
C(6) C(1) C(2) N(2) -178.1(3)
C(6) C(1) C(2) C(3) 0.9(3)
O(1) C(1) C(6) C(5) 176.9(4)
O(1) C(1) C(6) N(6) -0.8(3)
C(2) C(1) C(6) C(5) -0.9(3)
C(2) C(1) C(6) N(6) -178.6(3)
C(1) C(2) N(2) O(2) 15.0(3)
C(1) C(2) N(2) O(2') -164.6(4)
C(3) C(2) N(2) O(2) -164.1(4)
C(3) C(2) N(2) O(2') 16.4(3)
C(1) C(2) C(3) C(4) -0.7(3)
N(2) C(2) C(3) C(4) 178.3(3)
C(2) C(3) C(4) N(4) 179.7(3)
C(2) C(3) C(4) C(5) 0.4(3)
C(3) C(4) N(4) O(4) -6.1(3)
C(3) C(4) N(4) O(4') 174.4(4)
C(5) C(4) N(4) O(4) 173.2(4)
C(5) C(4) N(4) O(4') -6.3(3)
C(3) C(4) C(5) C(6) -0.4(3)
N(4) C(4) C(5) C(6) -179.7(4)
C(4) C(5) C(6) C(1) 0.7(3)
C(4) C(5) C(6) N(6) 178.4(3)
C(1) C(6) N(6) O(6) 142.3(4)
C(1) C(6) N(6) O(6') -35.7(4)
C(5) C(6) N(6) O(6) -35.5(4)
C(5) C(6) N(6) O(6') 146.5(4)
C(8A) N(1A) C(2A) C(3A) -1.0(3)
C(2A) N(1A) C(8A) C(7A) -179.0(4)
C(2A) N(1A) C(8A) C(9A) 0.8(3)
N(1A) C(2A) C(3A) C(10A) 179.1(4)
N(1A) C(2A) C(3A) C(9A) 0.8(3)
C(2A) C(3A) C(10A) C(11A) 104.5(4)
C(9A) C(3A) C(10A) C(11A) -77.6(3)
C(2A) C(3A) C(9A) C(4A) 178.3(4)
C(2A) C(3A) C(9A) C(8A) -0.3(3)
C(10A) C(3A) C(9A) C(4A) 0.1(4)
C(10A) C(3A) C(9A) C(8A) -178.5(3)
C(3A) C(10A) C(11A) O(12A) 12.2(4)
C(3A) C(10A) C(11A) N(12A) -168.1(3)
C(9A) C(4A) C(5A) C(6A) -1.2(4)
C(5A) C(4A) C(9A) C(3A) -178.0(4)
C(5A) C(4A) C(9A) C(8A) 0.4(3)
C(4A) C(5A) C(6A) C(7A) 1.0(4)
C(5A) C(6A) C(7A) C(8A) 0.1(4)
C(6A) C(7A) C(8A) N(1A) 178.8(4)
C(6A) C(7A) C(8A) C(9A) -0.9(4)
N(1A) C(8A) C(9A) C(3A) -0.3(3)
N(1A) C(8A) C(9A) C(4A) -179.1(3)
C(7A) C(8A) C(9A) C(3A) 179.5(3)
C(7A) C(8A) C(9A) C(4A) 0.7(3)
