data_2011185
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1026
_journal_page_last  1027
_publ_section_title
;
1H-Pyrrolo[2,3-b]pyridine-3-acetic acid as a molecular probe for use in auxin
physiology
;
loop_
_publ_author_name
  "Antoli\'c, Snje\<zana"
  "Koji\'c-Prodi\'c, Biserka"
  'Magnus, Volker'
_chemical_name_common  '7-aza-IAA'
_chemical_formula_moiety  'C9 H8 N2 O2'
_chemical_formula_sum  'C9 H8 N2 O2'
_chemical_formula_weight  176.17
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P n a 21'
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
_cell_length_a  14.9965(7)
_cell_length_b  4.2170(3)
_cell_length_c  26.0220(10)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1645.64(15)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.42220(10)
_diffrn_ambient_temperature  293(2)
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