#------------------------------------------------------------------------------
#$Date: 2022-09-28 18:08:17 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/15/2101508.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_2101508
loop_
_publ_author_name
'Nigović, B.'
'Kojić-Prodić, B.'
'Antolić, S.'
'Tomić, S.'
'Puntarec, V.'
'Cohen, J. D.'
_publ_section_title
;
 Structural studies on monohalogenated derivatives of the phytohormone
 indole-3-acetic acid (auxin)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              332
_journal_page_last               343
_journal_paper_doi               10.1107/S010876819500838X
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C10 H8 Br N O2'
_chemical_formula_weight         254.08
_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                116.02(3)
_cell_angle_beta                 92.67(5)
_cell_angle_gamma                100.12(4)
_cell_formula_units_Z            2
_cell_length_a                   5.645(3)
_cell_length_b                   9.713(4)
_cell_length_c                   10.019(4)
_cell_volume                     481.2(4)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    4.20
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             252
_cod_data_source_file            se0178.cif
_cod_data_source_block           se0178e
_cod_original_cell_volume        481.2(5)
_cod_original_formula_sum        'C10 H8 Br1 N1 O2'
_cod_database_code               2101508
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
Br .00865(4) .21409(3) .44576(3) .05900(10)
O1 -.2627(2) .97240(10) .8741(2) .0579(4)
O2 -.1475(2) .81910(10) .96420(10) .0493(3)
N1 -.7224(3) .3900(2) .8680(2) .0513(4)
C2 -.7263(3) .5356(2) .8808(2) .0511(4)
C3 -.5668(3) .5755(2) .8008(2) .0393(4)
C31 -.4522(3) .4447(2) .7312(2) .0365(4)
C4 -.2806(3) .4112(2) .6315(2) .0387(4)
C5 -.2172(3) .2694(2) .5860(2) .0409(4)
C6 -.3082(4) .1606(2) .6359(2) .0495(4)
C7 -.4798(4) .1910(2) .7325(2) .0498(4)
C71 -.5518(3) .3325(2) .7774(2) .0411(4)
C8 -.5170(3) .7246(2) .7896(2) .0445(4)
C9 -.2917(3) .8413(2) .8854(2) .0384(4)
H1 -.7940(9) .3375(8) .9195(8) .0938(9)
H2 -.8312(9) .5935(8) .9459(8) .0910(9)
H4 -.2043(8) .4869(8) .5964(8) .0461(9)
H6 -.2637(8) .0586(8) .5992(8) .0638(9)
H7 -.5486(8) .1152(8) .7666(8) .0600(9)
H11 -.1353(9) 1.0327(8) .9156(8) .0919(9)
H81 -.6583(9) .7709(8) .8121(8) .0687(9)
H82 -.5217(9) .7001(8) .6829(8) .0742(9)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C71 108.0(2)
N1 C2 C3 111.4(2)
C2 C3 C8 126.9(2)
C2 C3 C31 105.9(2)
C31 C3 C8 127.2(2)
C3 C31 C4 133.8(2)
C3 C31 C71 106.9(2)
C4 C31 C71 119.2(2)
C31 C4 C5 117.2(2)
C4 C5 C6 123.8(2)
C5 C6 C7 119.6(2)
C6 C7 C71 117.6(2)
C31 C71 C7 122.5(2)
N1 C71 C7 129.7(2)
N1 C71 C31 107.8(2)
C3 C8 C9 115.4(2)
C8 C9 O1 112.3(2)
C8 C9 O2 125.1(2)
O1 C9 O2 122.6(2)
C4 C5 Br 119.2(2)
C6 C5 Br 116.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.367(3)
N1 C71 1.374(2)
C2 C3 1.349(3)
C3 C31 1.440(3)
C4 C31 1.399(2)
C4 C5 1.368(3)
C5 C6 1.388(3)
C6 C7 1.378(3)
C7 C71 1.388(3)
C31 C71 1.403(3)
C3 C8 1.480(3)
C8 C9 1.500(3)
O1 C9 1.310(3)
O2 C9 1.218(2)
Br C5 1.906(2)
