#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/05/2220557.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_2220557
loop_
_publ_author_name
'Santos, Suseanne K. M.'
'Neves Filho, Ricardo A. W.'
'Bortoluzzi, Adailton J.'
'Srivastava, Rajendra M.'
_publ_section_title
;
 3-[3-(3-Fluorophenyl)-1,2,4-oxadiazol-5-yl]propionic acid
;
_journal_coeditor_code           IS2367
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o146
_journal_paper_doi               10.1107/S1600536808042001
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H9 F N2 O3'
_chemical_formula_moiety         'C11 H9 F N2 O3'
_chemical_formula_sum            'C11 H9 F N2 O3'
_chemical_formula_weight         236.20
_chemical_name_systematic
;
3-[3-(3-Fluorophenyl)-1,2,4-oxadiazol-5-yl]propionic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.769(5)
_cell_angle_beta                 87.965(7)
_cell_angle_gamma                81.252(7)
_cell_formula_units_Z            2
_cell_length_a                   5.0550(10)
_cell_length_b                   5.9050(10)
_cell_length_c                   17.9670(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.84
_cell_measurement_theta_min      5.01
_cell_volume                     528.47(14)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_molecular_graphics
'PLATON (Spek, 2003) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0100
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2136
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         1.14
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular plate'
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                1557
_reflns_number_total             2066
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2367.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220557
_cod_database_fobs_code          2220557
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
C C3 0.1073(3) -0.0359(3) 0.24108(9) 0.0403(4) Uani d . 1 . .
C C5 -0.1973(3) 0.0022(3) 0.32245(9) 0.0412(4) Uani d . 1 . .
C C6 -0.4105(3) 0.0731(3) 0.37879(10) 0.0463(4) Uani d . 1 . .
H H6A -0.3429 0.0278 0.4284 0.056 Uiso calc R 1 . .
H H6B -0.5616 -0.0064 0.3722 0.056 Uiso calc R 1 . .
C C7 -0.5043(3) 0.3291(3) 0.37270(10) 0.0476(4) Uani d . 1 . .
H H7A -0.3529 0.4086 0.3788 0.057 Uiso calc R 1 . .
H H7B -0.5738 0.3741 0.3233 0.057 Uiso calc R 1 . .
C C8 -0.7169(3) 0.4009(3) 0.42998(9) 0.0422(4) Uani d . 1 . .
C C11 0.3022(3) 0.0236(3) 0.18257(9) 0.0415(4) Uani d . 1 . .
C C12 0.2778(4) 0.2461(3) 0.15009(10) 0.0522(4) Uani d . 1 . .
H H12 0.1426 0.3584 0.1660 0.063 Uiso calc R 1 . .
C C13 0.4575(4) 0.2996(4) 0.09349(11) 0.0618(5) Uani d . 1 . .
H H13 0.4413 0.4485 0.0715 0.074 Uiso calc R 1 . .
C C14 0.6588(4) 0.1352(4) 0.06958(11) 0.0594(5) Uani d . 1 . .
H H14 0.7785 0.1708 0.0316 0.071 Uiso calc R 1 . .
C C15 0.6783(3) -0.0823(3) 0.10322(10) 0.0534(5) Uani d . 1 . .
C C16 0.5063(3) -0.1432(3) 0.15924(10) 0.0483(4) Uani d . 1 . .
H H16 0.5256 -0.2923 0.1811 0.058 Uiso calc R 1 . .
N N2 0.0849(3) -0.2473(3) 0.26222(9) 0.0552(4) Uani d . 1 . .
N N4 -0.0667(3) 0.1270(2) 0.27700(8) 0.0437(3) Uani d . 1 . .
O O1 -0.1230(2) -0.2237(2) 0.31750(7) 0.0555(4) Uani d . 1 . .
O O9 -0.8599(2) 0.2685(2) 0.45969(7) 0.0547(3) Uani d . 1 . .
O O10 -0.7395(3) 0.6168(2) 0.44456(8) 0.0551(3) Uani d . 1 . .
F F17 0.8776(2) -0.2448(2) 0.07982(7) 0.0822(4) Uani d . 1 . .
H H10 -0.885(6) 0.660(5) 0.4800(16) 0.102(8) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C3 N4 . . 114.80(14) ?
N2 C3 C11 . . 122.14(14) ?
N4 C3 C11 . . 123.06(14) ?
N4 C5 O1 . . 113.59(14) ?
N4 C5 C6 . . 129.61(15) ?
O1 C5 C6 . . 116.79(13) ?
C5 C6 C7 . . 112.30(13) ?
C5 C6 H6A . . 109.1 ?
C7 C6 H6A . . 109.1 ?
C5 C6 H6B . . 109.1 ?
C7 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.9 ?
C8 C7 C6 . . 112.31(14) ?
C8 C7 H7A . . 109.1 ?
C6 C7 H7A . . 109.1 ?
C8 C7 H7B . . 109.1 ?
C6 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.9 ?
O9 C8 O10 . . 123.07(15) ?
O9 C8 C7 . . 122.54(15) ?
O10 C8 C7 . . 114.38(14) ?
C12 C11 C16 . . 120.20(15) ?
C12 C11 C3 . . 119.61(15) ?
C16 C11 C3 . . 120.18(15) ?
C11 C12 C13 . . 119.36(17) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C14 C13 C12 . . 120.87(18) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C15 C14 C13 . . 118.25(17) ?
C15 C14 H14 . . 120.9 ?
C13 C14 H14 . . 120.9 ?
F17 C15 C14 . . 118.33(16) ?
F17 C15 C16 . . 118.68(18) ?
C14 C15 C16 . . 122.99(17) ?
C15 C16 C11 . . 118.33(17) ?
C15 C16 H16 . . 120.8 ?
C11 C16 H16 . . 120.8 ?
C3 N2 O1 . . 102.97(13) ?
C5 N4 C3 . . 102.40(13) ?
C5 O1 N2 . . 106.23(12) ?
C8 O10 H10 . . 112.6(16) ?
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
C3 N2 . 1.298(2) ?
C3 N4 . 1.382(2) ?
C3 C11 . 1.475(2) ?
C5 N4 . 1.291(2) ?
C5 O1 . 1.338(2) ?
C5 C6 . 1.486(2) ?
C6 C7 . 1.511(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.497(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 O9 . 1.2252(19) ?
C8 O10 . 1.308(2) ?
C11 C12 . 1.387(2) ?
C11 C16 . 1.389(2) ?
C12 C13 . 1.390(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.376(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.370(3) ?
C14 H14 . 0.9300 ?
C15 F17 . 1.359(2) ?
C15 C16 . 1.370(2) ?
C16 H16 . 0.9300 ?
N2 O1 . 1.4183(19) ?
O10 H10 . 0.97(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O10 H10 O9 2_366 0.97(3) 1.68(3) 2.650(2) 179(3) y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N4 C5 C6 C7 . . . . 8.6(3) ?
O1 C5 C6 C7 . . . . -172.42(15) ?
C5 C6 C7 C8 . . . . -179.36(14) ?
C6 C7 C8 O9 . . . . -23.4(2) ?
C6 C7 C8 O10 . . . . 157.66(15) ?
N2 C3 C11 C12 . . . . 165.28(17) ?
N4 C3 C11 C12 . . . . -14.0(2) ?
N2 C3 C11 C16 . . . . -13.6(2) ?
N4 C3 C11 C16 . . . . 167.08(15) ?
C16 C11 C12 C13 . . . . 0.7(3) ?
C3 C11 C12 C13 . . . . -178.15(17) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C13 C14 C15 . . . . -0.3(3) ?
C13 C14 C15 F17 . . . . -179.80(17) ?
C13 C14 C15 C16 . . . . 0.2(3) ?
F17 C15 C16 C11 . . . . -179.68(16) ?
C14 C15 C16 C11 . . . . 0.3(3) ?
C12 C11 C16 C15 . . . . -0.8(3) ?
C3 C11 C16 C15 . . . . 178.08(15) ?
N4 C3 N2 O1 . . . . -0.10(19) ?
C11 C3 N2 O1 . . . . -179.48(14) ?
O1 C5 N4 C3 . . . . -0.79(18) ?
C6 C5 N4 C3 . . . . 178.25(16) ?
N2 C3 N4 C5 . . . . 0.54(19) ?
C11 C3 N4 C5 . . . . 179.91(15) ?
N4 C5 O1 N2 . . . . 0.77(19) ?
C6 C5 O1 N2 . . . . -178.40(14) ?
C3 N2 O1 C5 . . . . -0.37(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12954303
