#------------------------------------------------------------------------------
#$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/70/2007080.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_2007080
loop_
_publ_author_name
'Okabe, Nobuo'
'Adachi, Yukari'
_publ_contact_author
; Nobuo Okabe
Faculty of Pharmaceutical Sciences
Kinki University
Kowakae 3-4-1
Higashiosaka
Osaka 577
Japan
;
_publ_section_title
;
 1<i>H</i>-Indole-3-propionic Acid
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              386
_journal_page_last               387
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C11 H11 N O2'
_chemical_formula_sum            'C11 H11 N O2'
_chemical_formula_weight         189.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_type_scat_source
'International Tables for X-ray Crystallography Vol.IV'
_cell_angle_alpha                90
_cell_angle_beta                 94.77(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.346(3)
_cell_length_b                   5.244(3)
_cell_length_c                   14.362(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      20.89
_cell_volume                     926.6(6)
_computing_cell_refinement
; MSC/AFC Diffractometer Control Software(Molecular Structure
Corporation, 1988)
;
_computing_data_collection
'MSC/AFC Diffractometer Control Software(Molecular Structure Corporation, 1988'
_computing_data_reduction
; TEXSAN. TEXRAY Structure Analysis Package (Molecular Srtucture
Corporation, 1985)
;
_computing_molecular_graphics    'ORTEPII(Johnson, 1976)'
_computing_structure_refinement
; TEXSAN. TEXRAY Structure Analysis Package (Molecular Structure
Corporation, 1985)
;
_computing_structure_solution
'MITHRIL (Gilmore, 1984) & DIRDIF (Beurskens, 1984)'
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.009
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2456
_diffrn_reflns_theta_max         27.45
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      'not determined'
_exptl_crystal_description       pillar
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.63
_refine_ls_hydrogen_treatment    ' refined isotropically'
_refine_ls_number_parameters     171
_refine_ls_number_reflns         1561
_refine_ls_R_factor_obs          .042
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 4F~o~^2^/\s^2^(F~o~^2^)'
_refine_ls_wR_factor_obs         .045
_reflns_number_observed          1561
_reflns_number_total             2353
_reflns_observed_criterion       I>1.50\s(I)
_[local]_cod_data_source_file    fr1089.cif
_[local]_cod_data_source_block   global
_[local]_cod_cif_authors_sg_H-M  'P 21/a'
_cod_original_cell_volume        926.6(5)
_cod_database_code               2007080
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-y,z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) .62740(10) .1331(2) .00115(9)
O(2) .48948(9) .2354(2) .08387(9)
N(1) .82380(10) 1.0810(3) .26360(10)
C(2) .78360(10) .8849(3) .20670(10)
C(3) .68080(10) .8253(3) .22610(10)
C(4) .56260(10) 1.0265(3) .34890(10)
C(5) .5633(2) 1.2153(4) .41580(10)
C(6) .6539(2) 1.3720(4) .43470(10)
C(7) .7459(2) 1.3447(4) .38830(10)
C(8) .74550(10) 1.1530(3) .32110(10)
C(9) .65500(10) .9950(3) .29970(10)
C(10) .60570(10) .6278(3) .18220(10)
C(11) .65610(10) .4707(3) .10840(10)
C(12) .58240(10) .2692(3) .06320(10)
H(1) .889(2) 1.149(4) .2610(10)
H(2) .8290(10) .808(4) .1610(10)
H(3) .571(2) -.017(5) -.032(2)
H(4) .5020(10) .918(4) .3380(10)
H(5) .499(2) 1.242(4) .4520(10)
H(6) .6530(10) 1.500(4) .4810(10)
H(7) .8060(10) 1.456(4) .4000(10)
H(10A) .5370(10) .713(3) .1530(10)
H(10B) .5840(10) .506(4) .2330(10)
H(11A) .6770(10) .584(4) .0560(10)
H(11B) .7250(10) .386(3) .1360(10)
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
O(1) .0483(7) .0476(7) .0489(7) -.0075(6) .0149(6) -.0171(6)
O(2) .0364(7) .0486(8) .0592(8) -.0075(6) .0094(6) -.0170(7)
N(1) .0314(7) .0480(10) .0630(10) -.0066(7) .0031(7) -.0130(8)
C(2) .0343(9) .0420(10) .0510(10) -.0002(8) .0049(8) -.0107(9)
C(3) .0327(8) .0302(8) .0374(8) .0009(7) .0024(6) -.0015(7)
C(4) .0410(10) .0380(10) .0430(10) -.0001(8) .0073(8) -.0004(8)
C(5) .0550(10) .0510(10) .0450(10) .0090(10) .0116(9) -.0030(10)
C(6) .0650(10) .0440(10) .0390(10) .0090(10) -.0037(9) -.0128(9)
C(7) .0460(10) .0380(10) .0490(10) .0002(8) -.0121(8) -.0070(8)
C(8) .0356(8) .0350(10) .0392(9) .0038(7) -.0043(7) -.0019(7)
C(9) .0351(8) .0283(8) .0329(8) .0022(6) -.0013(6) .0013(7)
C(10) .0325(8) .0325(9) .0406(9) -.0024(7) .0035(7) -.0047(7)
C(11) .0340(8) .0342(9) .0400(9) -.0028(7) .0052(7) -.0047(7)
C(12) .0351(8) .0328(8) .0331(8) -.0004(7) .0027(7) -.0002(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(12) . . 1.291(2) yes
O(2) C(12) . . 1.243(2) yes
N(1) C(2) . . 1.380(2) yes
N(1) C(8) . . 1.375(2) yes
C(2) C(3) . . 1.358(2) yes
C(3) C(9) . . 1.438(2) yes
C(3) C(10) . . 1.494(2) yes
C(4) C(5) . . 1.379(3) no
C(4) C(9) . . 1.401(2) no
C(5) C(6) . . 1.397(3) no
C(6) C(7) . . 1.372(3) no
C(7) C(8) . . 1.393(2) no
C(8) C(9) . . 1.405(2) no
C(10) C(11) . . 1.517(2) yes
C(11) C(12) . . 1.493(2) yes
O(1) H(3) . . 1.13(3) no
N(1) H(1) . . .88(2) no
C(2) H(2) . . .99(2) no
C(4) H(4) . . .94(2) no
C(5) H(5) . . .99(2) no
C(6) H(6) . . .94(2) no
C(7) H(7) . . .94(2) no
C(10) H(10A) . . 1.02(2) no
C(10) H(10B) . . 1.02(2) no
C(11) H(11A) . . 1.01(2) no
C(11) H(11B) . . 1.01(2) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) N(1) C(8) 108.90(10) yes
N(1) C(2) C(3) 110.2(2) yes
C(2) C(3) C(9) 106.10(10) yes
C(2) C(3) C(10) 129.10(10) yes
C(9) C(3) C(10) 124.80(10) yes
C(5) C(4) C(9) 118.6(2) no
C(4) C(5) C(6) 121.1(2) no
C(5) C(6) C(7) 121.8(2) no
C(6) C(7) C(8) 117.2(2) no
N(1) C(8) C(7) 130.7(2) yes
N(1) C(8) C(9) 107.00(10) yes
C(7) C(8) C(9) 122.2(2) no
C(3) C(9) C(4) 133.1(2) yes
C(3) C(9) C(8) 107.70(10) yes
C(4) C(9) C(8) 119.1(2) no
C(3) C(10) C(11) 113.30(10) yes
C(10) C(11) C(12) 115.10(10) yes
O(1) C(12) O(2) 122.50(10) yes
O(1) C(12) C(11) 113.80(10) yes
O(2) C(12) C(11) 122.30(10) yes
C(12) O(1) H(3) 114.0(10) no
C(2) N(1) H(1) 124.0(10) no
C(8) N(1) H(1) 127.0(10) no
N(1) C(2) H(2) 120.0(10) no
C(3) C(2) H(2) 130.0(10) no
C(5) C(4) H(4) 121.0(10) no
C(9) C(4) H(4) 121.0(10) no
C(4) C(5) H(5) 121.0(10) no
C(6) C(5) H(5) 118.0(10) no
C(5) C(6) H(6) 120.0(10) no
C(7) C(6) H(6) 118.0(10) no
C(6) C(7) H(7) 121.0(10) no
C(8) C(7) H(7) 122.0(10) no
C(3) C(10) H(10A) 110.0(10) no
C(3) C(10) H(10B) 109.0(10) no
C(11) C(10) H(10B) 108.0(10) no
H(10A) C(10) H(10B) 108.0(10) no
C(10) C(11) H(11A) 110.0(10) no
C(10) C(11) H(11B) 110.0(10) no
C(12) C(11) H(11A) 105.0(10) no
C(12) C(11) H(11B) 108.0(10) no
H(11A) C(11) H(11B) 107.0(10) no
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
_geom_torsion_publ_flag
O(1) C(12) C(11) C(10) -179.10(10) no
O(2) C(12) C(11) C(10) 0.3(2) no
N(1) C(2) C(3) C(9) 0.1(2) no
N(1) C(2) C(3) C(10) 179.7(2) no
N(1) C(8) C(7) C(6) 179.6(2) no
N(1) C(8) C(9) C(3) -0.6(2) no
N(1) C(8) C(9) C(4) 179.7(2) no
C(2) N(1) C(8) C(7) -178.1(2) no
C(2) N(1) C(8) C(9) 0.7(2) no
C(2) C(3) C(9) C(4) 180.0(2) no
C(2) C(3) C(9) C(8) 0.3(2) no
C(2) C(3) C(10) C(11) 2.3(3) no
C(3) C(2) N(1) C(8) -0.5(2) no
C(3) C(9) C(4) C(5) -178.6(2) no
C(3) C(9) C(8) C(7) 178.3(2) no
C(3) C(10) C(11) C(12) 179.50(10) no
C(4) C(5) C(6) C(7) -0.3(3) no
C(4) C(9) C(3) C(10) 0.3(3) no
C(4) C(9) C(8) C(7) -1.4(2) no
C(5) C(4) C(9) C(8) 1.0(2) no
C(5) C(6) C(7) C(8) -0.1(3) no
C(6) C(5) C(4) C(9) -0.2(3) no
C(6) C(7) C(8) C(9) 1.0(3) no
C(8) C(9) C(3) C(10) -179.3(2) no
C(9) C(3) C(10) C(11) -178.1(2) no