#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011185.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2011185
loop_
_publ_author_name
'Antoli\'c, Snje\<zana'
'Koji\'c-Prodi\'c, Biserka'
'Magnus, Volker'
_publ_section_title
;
1H-Pyrrolo[2,3-b]pyridine-3-acetic acid as a molecular probe for use in auxin
physiology
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              1026
_journal_page_last               1027
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C9 H8 N2 O2'
_chemical_formula_sum            'C9 H8 N2 O2'
_chemical_formula_weight         176.17
_chemical_name_common            7-aza-IAA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.9965(7)
_cell_length_b                   4.2170(3)
_cell_length_c                   26.0220(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1645.64(15)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.42220(10)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_database_code               2011185
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,1/2+z
1/2+x,1/2-y,z
1/2-x,1/2+y,1/2+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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C31 .4789(3) .3875(10) .21329(16) .0393(10) Uani d . 1 . . C
C4 .4889(3) .2704(12) .1642(2) .0530(12) Uani d . 1 . . C
H4 .5378 .1463 .1554 .064 Uiso calc R 1 . . H
C5 .4242(4) .3427(13) .1286(2) .0572(13) Uani d . 1 . . C
H5 .4290 .2653 .0952 .069 Uiso calc R 1 . . H
C6 .3523(4) .5297(13) .1421(2) .0543(12) Uani d . 1 . . C
H6 .3105 .5774 .1168 .065 Uiso calc R 1 . . H
N2 .3391(2) .6469(9) .18957(15) .0455(10) Uani d . 1 . . N
C71 .4026(3) .5737(11) .22313(17) .0411(11) Uani d . 1 . . C
N1 .4037(2) .6671(9) .27306(15) .0457(10) Uani d . 1 . . N
H1 .3643 .7826 .2880 .055 Uiso calc R 1 . . H
C2 .4794(3) .5436(11) .29547(19) .0465(12) Uani d . 1 . . C
H2 .4959 .5751 .3295 .056 Uiso calc R 1 . . H
C3 .5266(3) .3688(11) .26079(17) .0416(11) Uani d . 1 . . C
C8 .6128(3) .2005(11) .2706(2) .0506(12) Uani d . 1 . . C
H8A .6145 .0094 .2499 .061 Uiso calc R 1 . . H
H8B .6149 .1370 .3064 .061 Uiso calc R 1 . . H
C9 .6942(3) .3968(11) .2588(2) .0452(11) Uani d . 1 . . C
O1 .6991(2) .4892(9) .21113(13) .0564(8) Uani d . 1 . . O
H1A .7454 .5890 .2068 .085 Uiso calc R 1 . . H
O2 .7487(2) .4621(10) .29103(15) .0698(11) Uani d . 1 . . O
C312 .2850(3) .5514(9) .48132(17) .0392(11) Uani d . 1 . . C
C42 .2689(3) .6192(12) .53230(19) .0509(12) Uani d . 1 . . C
H42 .2196 .7395 .5418 .061 Uiso calc R 1 . . H
C52 .3270(4) .5062(14) .56906(19) .0604(13) Uani d . 1 . . C
H52 .3167 .5465 .6037 .072 Uiso calc R 1 . . H
C62 .4005(3) .3331(13) .55409(19) .0583(14) Uani d . 1 . . C
H62 .4391 .2620 .5796 .070 Uiso calc R 1 . . H
N22 .4198(2) .2607(9) .50541(16) .0465(10) Uani d . 1 . . N
C712 .3619(3) .3718(10) .47085(17) .0418(11) Uani d . 1 . . C
N12 .3675(2) .3284(9) .41905(14) .0453(10) Uani d . 1 . . N
H12 .4085 .2252 .4031 .054 Uiso calc R 1 . . H
C22 .2964(3) .4773(12) .39685(19) .0459(11) Uani d . 1 . . C
H22 .2851 .4811 .3617 .055 Uiso calc R 1 . . H
C32 .2444(3) .6189(11) .43277(18) .0419(11) Uani d . 1 . . C
C82 .1614(3) .8106(11) .4237(2) .0531(14) Uani d . 1 . . C
H82A .1606 .8830 .3883 .064 Uiso calc R 1 . . H
H82B .1624 .9962 .4457 .064 Uiso calc R 1 . . H
C92 .0772(3) .6229(11) .4343(2) .0475(12) Uani d . 1 . . C
O12 .0647(2) .5692(9) .48320(13) .0657(11) Uani d . 1 . . O
H12A .0190 .4648 .4871 .099 Uiso calc R 1 . . H
O22 .0288(2) .5275(9) .40090(14) .0687(11) Uani d . 1 . . O
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
C31 .039(2) .034(2) .045(3) -.0079(18) .001(2) -.003(2)
C4 .045(3) .053(3) .061(3) -.001(2) .005(3) -.014(2)
C5 .059(3) .067(4) .045(3) .000(3) .001(3) -.016(2)
C6 .048(3) .070(3) .045(3) -.005(2) -.007(2) -.006(2)
N2 .039(2) .054(2) .044(2) -.0074(17) .000(2) -.0017(18)
C71 .030(2) .053(3) .040(3) -.0080(18) .003(2) .003(2)
N1 .037(2) .056(2) .043(2) .0008(17) .0074(18) -.0082(18)
C2 .038(3) .054(3) .047(3) -.010(2) .000(2) -.003(2)
C3 .035(2) .043(2) .046(3) -.0046(19) -.003(2) .000(2)
C8 .050(3) .047(3) .055(3) -.004(2) -.007(3) .011(2)
C9 .037(2) .048(3) .051(3) .005(2) .000(2) .007(2)
O1 .047(2) .075(2) .0473(19) -.0084(18) -.0003(17) .0083(18)
O2 .0544(19) .093(3) .062(3) -.020(2) -.008(2) .021(2)
C312 .034(2) .040(2) .043(2) -.0109(18) .004(2) -.003(2)
C42 .049(3) .057(3) .046(3) -.002(2) .009(3) -.007(2)
C52 .061(3) .082(4) .037(3) -.008(3) .005(3) -.008(3)
C62 .055(3) .074(4) .045(3) -.006(3) -.006(3) .004(2)
N22 .039(2) .053(2) .048(2) -.0030(18) -.002(2) .0031(19)
C712 .035(3) .047(2) .043(3) -.007(2) .006(2) .000(2)
N12 .0333(19) .061(3) .041(2) .0004(17) .0042(19) -.0053(18)
C22 .044(3) .056(3) .037(2) -.007(2) .003(2) .000(2)
C32 .040(2) .039(2) .047(3) -.0101(19) .002(2) .003(2)
C82 .046(3) .042(3) .072(4) .001(2) -.004(3) .008(2)
C92 .040(3) .043(2) .060(4) .009(2) .002(3) .007(2)
O12 .048(2) .093(3) .056(2) -.0171(19) .0004(19) -.007(2)
O22 .056(2) .096(3) .054(2) -.019(2) -.008(2) .013(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C31 C4 . 1.378(6) yes
C31 C71 . 1.410(6) yes
C31 C3 . 1.431(6) yes
C4 C5 . 1.375(7) yes
C5 C6 . 1.382(7) yes
C6 N2 . 1.345(6) yes
N2 C71 . 1.329(6) yes
C71 N1 . 1.358(6) yes
N1 C2 . 1.377(5) yes
C2 C3 . 1.364(6) yes
C3 C8 . 1.497(6) yes
C8 C9 . 1.505(6) yes
C9 O2 . 1.204(5) yes
C9 O1 . 1.301(6) yes
C312 C42 . 1.378(6) yes
C312 C712 . 1.407(6) yes
C312 C32 . 1.431(6) yes
C42 C52 . 1.378(7) yes
C52 C62 . 1.378(7) yes
C62 N22 . 1.335(6) yes
N22 C712 . 1.334(6) yes
C712 N12 . 1.363(6) yes
N12 C22 . 1.366(6) yes
C22 C32 . 1.355(6) yes
C32 C82 . 1.503(6) yes
C82 C92 . 1.515(7) yes
C92 O22 . 1.202(6) yes
C92 O12 . 1.306(6) yes