#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228712.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_2228712
loop_
_publ_author_name
'Zhang, Fang'
'Liu, Fei'
'Chen, Qifan'
'Dong, Mingdong'
_publ_section_title
;
 3-[3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl]propanoic acid
;
_journal_coeditor_code           FK2032
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o193
_journal_paper_doi               10.1107/S1600536810051639
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H9 N3 O3'
_chemical_formula_moiety         'C10 H9 N3 O3'
_chemical_formula_sum            'C10 H9 N3 O3'
_chemical_formula_weight         219.20
_chemical_name_systematic
;
3-[3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl]propanoic acid
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1298(12)
_cell_length_b                   6.8194(14)
_cell_length_c                   23.426(5)
_cell_measurement_reflns_used    6383
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.11
_cell_volume                     979.2(3)
_computing_cell_refinement       'XSCANS (Bruker, 2003)'
_computing_data_collection       'XSCANS (Bruker, 2003)'
_computing_data_reduction
'XSCANS (Bruker, 2003) and SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8147
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1138
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0339
_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)+(0.0487P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                884
_reflns_number_total             1138
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fk2032.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom and difmap' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               2228712
_cod_database_fobs_code          2228712
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
O O3 0.8809(3) 0.4377(3) 0.16313(7) 0.0450(5) Uani d . 1 . .
O O1 0.4239(4) 0.4072(4) 0.33554(8) 0.0628(6) Uani d . 1 . .
H H1 0.3237 0.4277 0.3579 0.094 Uiso calc R 1 . .
O O2 0.2140(4) 0.5819(3) 0.27757(9) 0.0681(7) Uani d . 1 . .
N N3 0.8817(4) 0.5436(3) -0.08242(9) 0.0468(6) Uani d . 1 . .
C C10 0.8297(5) 0.5499(4) -0.02742(11) 0.0412(6) Uani d . 1 . .
H H10 0.6895 0.5885 -0.0173 0.049 Uiso calc R 1 . .
N N2 0.6960(4) 0.5622(3) 0.09157(9) 0.0394(5) Uani d . 1 . .
N N1 1.0181(4) 0.4195(3) 0.11489(9) 0.0461(5) Uani d . 1 . .
C C6 0.9757(4) 0.5012(4) 0.01552(11) 0.0358(5) Uani d . 1 . .
C C5 0.8992(4) 0.4978(3) 0.07499(10) 0.0346(5) Uani d . 1 . .
C C1 0.3807(5) 0.4921(4) 0.28656(12) 0.0430(6) Uani d . 1 . .
C C2 0.5595(4) 0.4565(4) 0.24436(11) 0.0426(6) Uani d . 1 . .
H H2A 0.5711 0.3167 0.2373 0.051 Uiso calc R 1 . .
H H2B 0.6967 0.5002 0.2606 0.051 Uiso calc R 1 . .
C C3 0.5225(5) 0.5608(4) 0.18853(10) 0.0427(6) Uani d . 1 . .
H H3A 0.3826 0.5204 0.1731 0.051 Uiso calc R 1 . .
H H3B 0.5153 0.7008 0.1956 0.051 Uiso calc R 1 . .
C C8 1.2425(5) 0.4437(4) -0.05639(12) 0.0491(7) Uani d . 1 . .
H H8 1.3826 0.4088 -0.0677 0.059 Uiso calc R 1 . .
C C7 1.1881(4) 0.4503(4) 0.00047(12) 0.0449(6) Uani d . 1 . .
H H7 1.2912 0.4214 0.0284 0.054 Uiso calc R 1 . .
C C4 0.6937(4) 0.5226(3) 0.14541(10) 0.0358(5) Uani d . 1 . .
C C9 1.0850(5) 0.4898(4) -0.09637(13) 0.0497(7) Uani d . 1 . .
H H9 1.1220 0.4832 -0.1348 0.060 Uiso calc R 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'
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
C4 O3 N1 . . 107.29(18) ?
C1 O1 H1 . . 109.5 ?
C10 N3 C9 . . 117.9(2) ?
N3 C10 C6 . . 122.8(3) ?
N3 C10 H10 . . 118.6 ?
C6 C10 H10 . . 118.6 ?
C4 N2 C5 . . 102.6(2) ?
C5 N1 O3 . . 101.84(19) ?
C10 C6 C7 . . 118.6(2) ?
C10 C6 C5 . . 119.1(2) ?
C7 C6 C5 . . 122.3(2) ?
N1 C5 N2 . . 115.8(2) ?
N1 C5 C6 . . 120.6(2) ?
N2 C5 C6 . . 123.4(2) ?
O2 C1 O1 . . 123.1(3) ?
O2 C1 C2 . . 125.9(3) ?
O1 C1 C2 . . 111.0(2) ?
C1 C2 C3 . . 112.8(2) ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
C4 C3 C2 . . 113.7(2) ?
C4 C3 H3A . . 108.8 ?
C2 C3 H3A . . 108.8 ?
C4 C3 H3B . . 108.8 ?
C2 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
C7 C8 C9 . . 118.7(3) ?
C7 C8 H8 . . 120.6 ?
C9 C8 H8 . . 120.6 ?
C8 C7 C6 . . 118.7(2) ?
C8 C7 H7 . . 120.6 ?
C6 C7 H7 . . 120.6 ?
N2 C4 O3 . . 112.4(2) ?
N2 C4 C3 . . 129.6(3) ?
O3 C4 C3 . . 117.9(2) ?
N3 C9 C8 . . 123.2(3) ?
N3 C9 H9 . . 118.4 ?
C8 C9 H9 . . 118.4 ?
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
O3 C4 . 1.351(3) ?
O3 N1 . 1.414(3) ?
O1 C1 . 1.312(3) ?
O1 H1 . 0.8200 ?
O2 C1 . 1.210(3) ?
N3 C10 . 1.328(4) ?
N3 C9 . 1.340(4) ?
C10 C6 . 1.387(4) ?
C10 H10 . 0.9300 ?
N2 C4 . 1.290(3) ?
N2 C5 . 1.377(3) ?
N1 C5 . 1.300(3) ?
C6 C7 . 1.393(4) ?
C6 C5 . 1.470(4) ?
C1 C2 . 1.496(4) ?
C2 C3 . 1.506(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.480(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C8 C7 . 1.374(4) ?
C8 C9 . 1.381(4) ?
C8 H8 . 0.9300 ?
C7 H7 . 0.9300 ?
C9 H9 . 0.9300 ?
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
O1 H1 N3 2_665 0.82 1.89 2.704(3) 172
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
C9 N3 C10 C6 . . . . -0.8(4) ?
C4 O3 N1 C5 . . . . 1.1(2) ?
N3 C10 C6 C7 . . . . 2.4(4) ?
N3 C10 C6 C5 . . . . -175.4(2) ?
O3 N1 C5 N2 . . . . -1.3(3) ?
O3 N1 C5 C6 . . . . -176.9(2) ?
C4 N2 C5 N1 . . . . 1.0(3) ?
C4 N2 C5 C6 . . . . 176.4(2) ?
C10 C6 C5 N1 . . . . 167.5(2) ?
C7 C6 C5 N1 . . . . -10.2(3) ?
C10 C6 C5 N2 . . . . -7.7(3) ?
C7 C6 C5 N2 . . . . 174.6(2) ?
O2 C1 C2 C3 . . . . 5.1(4) ?
O1 C1 C2 C3 . . . . -176.8(2) ?
C1 C2 C3 C4 . . . . -178.1(2) ?
C9 C8 C7 C6 . . . . 0.7(4) ?
C10 C6 C7 C8 . . . . -2.3(4) ?
C5 C6 C7 C8 . . . . 175.4(2) ?
C5 N2 C4 O3 . . . . -0.2(3) ?
C5 N2 C4 C3 . . . . 178.2(2) ?
N1 O3 C4 N2 . . . . -0.6(3) ?
N1 O3 C4 C3 . . . . -179.1(2) ?
C2 C3 C4 N2 . . . . 168.1(2) ?
C2 C3 C4 O3 . . . . -13.6(3) ?
C10 N3 C9 C8 . . . . -0.9(4) ?
C7 C8 C9 N3 . . . . 0.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2411410
