#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508155.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_4508155
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_formula_sum            'C11 H10 N2 O3'
_chemical_formula_weight         218.21
_chemical_name_systematic
;
 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoic acid
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-08-14T14:37:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.9820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2014(2)
_cell_length_b                   14.0392(3)
_cell_length_c                   11.8806(2)
_cell_measurement_temperature    173(2)
_cell_volume                     2030.21(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32856
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.4405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                3679
_reflns_number_total             5044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400649h_si_004.cif
_cod_data_source_block           200612
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4508155
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O4 O 0.85408(7) 0.05774(7) 0.17085(7) 0.0251(2) Uani 1 1 d
C6 C 0.05484(10) 0.19784(9) 0.77450(10) 0.0218(3) Uani 1 1 d
C16 C 0.54660(10) 0.12908(9) -0.01543(10) 0.0239(3) Uani 1 1 d
C2 C 0.17179(10) 0.19236(9) 0.75751(10) 0.0214(3) Uani 1 1 d
C11 C 0.02061(12) 0.21688(10) 0.88156(11) 0.0292(3) Uani 1 1 d
C17 C 1.04787(10) 0.05596(9) 0.23468(10) 0.0223(3) Uani 1 1 d
C7 C -0.02292(11) 0.18241(10) 0.68505(11) 0.0271(3) Uani 1 1 d
C8 C -0.13386(11) 0.18578(10) 0.70302(12) 0.0302(3) Uani 1 1 d
C18 C 1.07740(12) 0.06934(10) 0.12472(11) 0.0281(3) Uani 1 1 d
C22 C 1.12931(11) 0.04797(10) 0.32255(11) 0.0283(3) Uani 1 1 d
C1 C 0.31445(10) 0.17720(9) 0.66501(10) 0.0222(3) Uani 1 1 d
C15 C 0.65788(11) 0.11844(10) 0.04646(11) 0.0257(3) Uani 1 1 d
C13 C 0.93276(10) 0.05237(9) 0.25920(10) 0.0222(3) Uani 1 1 d
C3 C 0.37604(11) 0.16154(12) 0.56394(11) 0.0303(3) Uani 1 1 d
C14 C 0.65243(12) 0.06082(12) 0.15388(12) 0.0308(3) Uani 1 1 d
C21 C 1.23860(12) 0.05350(11) 0.29910(12) 0.0319(3) Uani 1 1 d
C5 C 0.55386(10) 0.11533(9) 0.48786(10) 0.0250(3) Uani 1 1 d
C4 C 0.49787(11) 0.14687(11) 0.59072(11) 0.0261(3) Uani 1 1 d
C9 C -0.16778(12) 0.20363(10) 0.80952(13) 0.0319(3) Uani 1 1 d
C19 C 1.18723(12) 0.07597(11) 0.10290(12) 0.0326(3) Uani 1 1 d
C12 C 0.75864(10) 0.05730(9) 0.22275(11) 0.0238(3) Uani 1 1 d
C10 C -0.09020(12) 0.21891(11) 0.89836(12) 0.0350(3) Uani 1 1 d
C20 C 1.26777(12) 0.06790(10) 0.19010(12) 0.0319(3) Uani 1 1 d
N2 N 0.25424(9) 0.19249(8) 0.83153(9) 0.0275(3) Uani 1 1 d
N4 N 0.88989(9) 0.04760(9) 0.35525(9) 0.0279(3) Uani 1 1 d
N1 N 0.34855(9) 0.18277(8) 0.77007(9) 0.0250(2) Uani 1 1 d
N3 N 0.77541(9) 0.05140(8) 0.33069(9) 0.0276(3) Uani 1 1 d
O1 O 0.20360(7) 0.18328(6) 0.65006(7) 0.0242(2) Uani 1 1 d
O3 O 0.66262(8) 0.11945(8) 0.50375(8) 0.0339(2) Uani 1 1 d
O2 O 0.50647(8) 0.08744(8) 0.40173(8) 0.0347(2) Uani 1 1 d
O6 O 0.55227(8) 0.16819(8) -0.11634(8) 0.0359(3) Uani 1 1 d
O5 O 0.46162(8) 0.10730(8) 0.02271(8) 0.0379(3) Uani 1 1 d
H3 H 0.5110(12) 0.0947(11) 0.6454(13) 0.035(4) Uiso 1 1 d
H5 H 0.0757(13) 0.2288(10) 0.9423(12) 0.034(4) Uiso 1 1 d
H14 H 1.0190(13) 0.0754(11) 0.0642(13) 0.038(4) Uiso 1 1 d
H4 H 0.5330(13) 0.2039(11) 0.6241(13) 0.037(4) Uiso 1 1 d
H17 H 1.2943(13) 0.0468(11) 0.3596(13) 0.038(4) Uiso 1 1 d
H12 H 0.6847(13) 0.1831(12) 0.0622(13) 0.037(4) Uiso 1 1 d
H18 H 1.1081(13) 0.0374(11) 0.3963(13) 0.036(4) Uiso 1 1 d
H13 H 0.7069(13) 0.0906(11) -0.0062(13) 0.037(4) Uiso 1 1 d
H8 H -0.1851(14) 0.1717(11) 0.6417(14) 0.040(4) Uiso 1 1 d
H7 H -0.2446(13) 0.2055(10) 0.8219(12) 0.033(4) Uiso 1 1 d
H2 H 0.3643(14) 0.2140(12) 0.5130(14) 0.044(5) Uiso 1 1 d
H6 H -0.1147(14) 0.2342(12) 0.9709(15) 0.049(5) Uiso 1 1 d
H9 H 0.0004(12) 0.1662(11) 0.6159(13) 0.031(4) Uiso 1 1 d
H10 H 0.5991(14) 0.0875(12) 0.2018(14) 0.046(5) Uiso 1 1 d
H1 H 0.3450(14) 0.1046(13) 0.5257(14) 0.053(5) Uiso 1 1 d
H15 H 1.2070(13) 0.0882(11) 0.0306(14) 0.039(4) Uiso 1 1 d
H16 H 1.3443(14) 0.0720(11) 0.1732(13) 0.043(4) Uiso 1 1 d
H11 H 0.6311(15) -0.0052(14) 0.1333(14) 0.056(5) Uiso 1 1 d
H1O H 0.6929(18) 0.0943(15) 0.4424(18) 0.080(7) Uiso 1 1 d
H2O H 0.4833(17) 0.1747(14) -0.1512(16) 0.063(6) 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
C12 O4 C13 103.23(9)
C7 C6 C11 119.72(12)
C7 C6 C2 120.56(12)
C11 C6 C2 119.71(11)
O5 C16 O6 123.25(12)
O5 C16 C15 124.32(12)
O6 C16 C15 112.40(11)
N2 C2 O1 112.25(11)
N2 C2 C6 129.10(11)
O1 C2 C6 118.62(10)
C10 C11 C6 119.67(13)
C18 C17 C22 119.73(12)
C18 C17 C13 120.60(11)
C22 C17 C13 119.65(11)
C8 C7 C6 119.90(13)
C9 C8 C7 120.36(13)
C19 C18 C17 120.10(12)
C21 C22 C17 119.43(13)
N1 C1 O1 112.03(11)
N1 C1 C3 130.35(12)
O1 C1 C3 117.56(11)
C16 C15 C14 111.91(11)
N4 C13 O4 111.95(11)
N4 C13 C17 129.45(11)
O4 C13 C17 118.55(10)
C1 C3 C4 113.42(11)
C12 C14 C15 113.21(11)
C20 C21 C22 120.78(13)
O2 C5 O3 123.39(12)
O2 C5 C4 124.48(12)
O3 C5 C4 112.11(11)
C5 C4 C3 111.32(11)
C8 C9 C10 119.60(13)
C20 C19 C18 120.05(13)
N3 C12 O4 111.82(11)
N3 C12 C14 128.57(12)
O4 C12 C14 119.59(11)
C11 C10 C9 120.74(13)
C21 C20 C19 119.90(13)
C2 N2 N1 105.81(10)
C13 N4 N3 105.80(10)
C1 N1 N2 106.65(10)
C12 N3 N4 107.19(10)
C1 O1 C2 103.25(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C12 1.3549(15)
O4 C13 1.3745(14)
C6 C7 1.3915(18)
C6 C11 1.3920(18)
C6 C2 1.4571(18)
C16 O5 1.1996(15)
C16 O6 1.3247(15)
C16 C15 1.5059(17)
C2 N2 1.2893(16)
C2 O1 1.3658(15)
C11 C10 1.381(2)
C17 C18 1.3918(18)
C17 C22 1.3949(18)
C17 C13 1.4550(18)
C7 C8 1.386(2)
C8 C9 1.381(2)
C18 C19 1.386(2)
C22 C21 1.383(2)
C1 N1 1.2903(16)
C1 O1 1.3545(15)
C1 C3 1.4766(18)
C15 C14 1.5163(19)
C13 N4 1.2896(16)
C3 C4 1.5125(19)
C14 C12 1.4847(18)
C21 C20 1.381(2)
C5 O2 1.2053(15)
C5 O3 1.3286(16)
C5 C4 1.5073(18)
C9 C10 1.385(2)
C19 C20 1.382(2)
C12 N3 1.2871(16)
N2 N1 1.4116(15)
N4 N3 1.4080(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146602
