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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508154.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4508154
loop_
_publ_author_name
'Gutov, Oleksii V.'
_publ_section_title
;
 1,3,4-Oxadiazoles for Crystal Engineering. Convenient Synthesis and
 Self-Assembly: Nonchiral Chains versus Chiral Helices
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3953
_journal_paper_doi               10.1021/cg400649h
_journal_volume                  13
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_sum            'C8 H10 N2 O3'
_chemical_formula_weight         182.18
_chemical_name_systematic
;
 3-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)propanoic acid
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-08-14T13:53:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.921(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0880(2)
_cell_length_b                   11.8516(4)
_cell_length_c                   14.0429(5)
_cell_measurement_temperature    173(2)
_cell_volume                     842.28(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6890
_diffrn_reflns_theta_full        28.85
_diffrn_reflns_theta_max         28.85
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_coef       0.0144(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0276P)²+0.1243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.068
_refine_ls_wR_factor_ref         0.0755
_reflns_number_gt                3396
_reflns_number_total             3799
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400649h_si_003.cif
_cod_data_source_block           1906122
_cod_database_code               4508154
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
C13 C 0.8292(3) 0.56107(15) 0.48349(14) 0.0212(4) Uani 1 1 d
C4 C 0.5498(3) 0.95909(16) 1.13752(14) 0.0206(4) Uani 1 1 d
C11 C 1.1693(4) 0.43522(17) 0.57731(15) 0.0248(4) Uani 1 1 d
C2 C 0.5402(3) 0.86681(14) 0.97694(12) 0.0181(4) Uani 1 1 d
C10 C 0.9943(3) 0.34784(15) 0.61193(12) 0.0193(4) Uani 1 1 d
C12 C 1.0650(4) 0.48428(17) 0.48107(15) 0.0239(4) Uani 1 1 d
C3 C 0.3952(3) 0.94018(16) 1.03967(14) 0.0206(4) Uani 1 1 d
C1 C 0.6102(3) 0.77838(14) 0.84880(13) 0.0199(4) Uani 1 1 d
C5 C 0.7920(3) 1.03270(14) 1.13881(13) 0.0184(4) Uani 1 1 d
C14 C 0.8613(4) 0.17800(16) 0.80583(14) 0.0262(4) Uani 1 1 d
C9 C 0.8587(3) 0.23440(15) 0.71390(13) 0.0195(4) Uani 1 1 d
C7 C 0.2842(4) 0.74509(18) 0.69992(15) 0.0307(5) Uani 1 1 d
C6 C 0.5625(4) 0.74206(17) 0.74943(13) 0.0233(4) Uani 1 1 d
C8 C 0.4791(4) 0.82837(18) 0.67253(15) 0.0313(5) Uani 1 1 d
C15 C 0.6206(4) 0.1128(2) 0.82764(16) 0.0348(5) Uani 1 1 d
C16 C 0.8633(4) 0.05022(17) 0.80987(17) 0.0356(5) Uani 1 1 d
O4 O 1.0565(2) 0.30812(10) 0.70264(8) 0.0207(3) Uani 1 1 d
O1 O 0.4374(2) 0.85183(10) 0.88428(9) 0.0198(3) Uani 1 1 d
O2 O 0.9744(2) 1.02745(12) 1.20024(9) 0.0286(3) Uani 1 1 d
O6 O 0.7336(3) 0.59009(13) 0.55415(10) 0.0351(4) Uani 1 1 d
O5 O 0.7421(3) 0.59447(11) 0.39532(10) 0.0253(3) Uani 1 1 d
O3 O 0.7817(2) 1.10744(12) 1.06748(9) 0.0248(3) Uani 1 1 d
N3 N 0.7853(3) 0.30232(14) 0.57019(11) 0.0225(3) Uani 1 1 d
N4 N 0.6942(3) 0.22756(13) 0.63787(11) 0.0211(3) Uani 1 1 d
N2 N 0.7985(3) 0.75195(13) 0.91267(11) 0.0227(3) Uani 1 1 d
N1 N 0.7535(3) 0.81011(13) 0.99771(11) 0.0227(3) Uani 1 1 d
H14 H 0.963(4) 0.2134(17) 0.8534(14) 0.021(5) Uiso 1 1 d
H16 H 0.974(4) 0.017(2) 0.8601(17) 0.034(6) Uiso 1 1 d
H10 H 1.184(5) 0.491(2) 0.6236(19) 0.048(7) Uiso 1 1 d
H17 H 0.467(4) 0.114(2) 0.7744(14) 0.031(5) Uiso 1 1 d
H7 H 0.450(4) 0.902(2) 0.6896(16) 0.034(6) Uiso 1 1 d
H4 H 0.434(4) 0.9960(16) 1.1821(14) 0.023(5) Uiso 1 1 d
H5 H 0.678(4) 0.6862(19) 0.7309(15) 0.034(6) Uiso 1 1 d
H13 H 1.201(4) 0.5293(19) 0.4527(14) 0.027(5) Uiso 1 1 d
H3 H 0.611(5) 0.885(2) 1.1727(19) 0.054(7) Uiso 1 1 d
H11 H 1.354(5) 0.402(2) 0.5718(15) 0.039(6) Uiso 1 1 d
H15 H 0.862(4) 0.0118(18) 0.7387(16) 0.027(5) Uiso 1 1 d
H2 H 0.349(4) 1.012(2) 1.0072(16) 0.033(6) Uiso 1 1 d
H12 H 1.014(4) 0.430(2) 0.4325(17) 0.040(6) Uiso 1 1 d
H8 H 0.239(5) 0.687(2) 0.6543(17) 0.037(6) Uiso 1 1 d
H18 H 0.584(4) 0.118(2) 0.8885(17) 0.034(6) Uiso 1 1 d
H1 H 0.220(4) 0.9043(18) 1.0451(14) 0.029(6) Uiso 1 1 d
H6 H 0.559(4) 0.819(2) 0.6099(17) 0.040(6) Uiso 1 1 d
H9 H 0.136(5) 0.7697(19) 0.7340(17) 0.042(7) Uiso 1 1 d
H1O H 0.932(5) 1.149(2) 1.0805(17) 0.051(7) Uiso 1 1 d
H2O H 0.621(5) 0.637(2) 0.4010(18) 0.051(8) Uiso 1 1 d
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 0 '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 0.006 '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
O6 C13 O5 124.01(17)
O6 C13 C12 125.64(17)
O5 C13 C12 110.34(16)
C5 C4 C3 116.08(16)
C10 C11 C12 113.19(16)
N1 C2 O1 112.39(15)
N1 C2 C3 129.11(16)
O1 C2 C3 118.47(14)
N3 C10 O4 112.58(15)
N3 C10 C11 130.12(17)
O4 C10 C11 117.30(15)
C13 C12 C11 114.67(17)
C2 C3 C4 112.20(15)
N2 C1 O1 111.28(16)
N2 C1 C6 129.57(16)
O1 C1 C6 119.15(15)
O2 C5 O3 122.73(16)
O2 C5 C4 123.25(17)
O3 C5 C4 113.97(15)
C9 C14 C15 118.95(17)
C9 C14 C16 119.51(18)
C15 C14 C16 58.81(15)
N4 C9 O4 111.75(15)
N4 C9 C14 130.72(17)
O4 C9 C14 117.52(15)
C8 C7 C6 60.92(13)
C1 C6 C7 119.30(17)
C1 C6 C8 119.34(17)
C7 C6 C8 58.43(13)
C7 C8 C6 60.65(13)
C16 C15 C14 60.92(14)
C15 C16 C14 60.27(15)
C9 O4 C10 103.19(13)
C2 O1 C1 103.45(13)
C10 N3 N4 105.74(14)
C9 N4 N3 106.72(14)
C1 N2 N1 107.24(14)
C2 N1 N2 105.63(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C13 O6 1.200(2)
C13 O5 1.332(2)
C13 C12 1.509(2)
C4 C5 1.508(2)
C4 C3 1.528(3)
C11 C10 1.480(3)
C11 C12 1.516(3)
C2 N1 1.284(2)
C2 O1 1.363(2)
C2 C3 1.487(3)
C10 N3 1.279(2)
C10 O4 1.364(2)
C1 N2 1.282(2)
C1 O1 1.368(2)
C1 C6 1.457(3)
C5 O2 1.202(2)
C5 O3 1.334(2)
C14 C9 1.453(3)
C14 C15 1.506(3)
C14 C16 1.516(3)
C9 N4 1.290(2)
C9 O4 1.354(2)
C7 C8 1.478(3)
C7 C6 1.512(3)
C6 C8 1.516(3)
C15 C16 1.483(3)
N3 N4 1.412(2)
N2 N1 1.418(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146601
