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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/4/50/81/4508156.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_4508156
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            'C8 H10 N2 O3'
_chemical_formula_weight         182.18
_chemical_name_systematic
;
 (2Z)-3-(5-isopropyl-1,3,4-oxadiazol-2-yl)propenoic acid
;
_space_group_IT_number           2
_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_date             2012-08-14T13:23:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                92.926(16)
_cell_angle_beta                 91.192(15)
_cell_angle_gamma                105.216(15)
_cell_formula_units_Z            4
_cell_length_a                   7.901(2)
_cell_length_b                   9.800(3)
_cell_length_c                   12.291(3)
_cell_measurement_temperature    173(2)
_cell_volume                     916.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13881
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9611
_exptl_absorpt_correction_T_min  0.9271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.1102
_refine_ls_shift/su_max          1.551
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1845P)²+1.9983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2918
_refine_ls_wR_factor_ref         0.3263
_reflns_number_gt                2137
_reflns_number_total             3226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400649h_si_005.cif
_cod_data_source_block           140612
_cod_database_code               4508156
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags
C9 C 0.2199(7) 0.6201(6) 0.7845(4) 0.0302(12) Uani 1 1 d .
C1 C 0.2752(6) 0.3988(6) 0.2784(4) 0.0280(12) Uani 1 1 d .
C10 C 0.1546(7) 0.7863(5) 0.7032(4) 0.0276(12) Uani 1 1 d .
C13 C 0.2764(7) 0.3829(5) 0.6171(4) 0.0289(12) Uani 1 1 d .
C5 C 0.2239(7) 0.6324(5) 0.1297(4) 0.0283(12) Uani 1 1 d .
C11 C 0.2901(7) 0.4981(6) 0.8066(4) 0.0303(12) Uani 1 1 d .
C2 C 0.3315(7) 0.2318(5) 0.1784(4) 0.0285(12) Uani 1 1 d .
C3 C 0.2124(7) 0.5237(6) 0.3109(4) 0.0302(12) Uani 1 1 d .
C4 C 0.1849(7) 0.6197(6) 0.2457(4) 0.0326(13) Uani 1 1 d .
C12 C 0.3178(7) 0.3996(6) 0.7350(4) 0.0315(12) Uani 1 1 d .
C6 C 0.3463(8) 0.1503(6) 0.0759(4) 0.0364(13) Uani 1 1 d .
H6 H 0.4621 0.1911 0.0469 0.044 Uiso 1 1 calc R
C14 C 0.1339(8) 0.8690(6) 0.6081(4) 0.0402(14) Uani 1 1 d .
H14 H 0.0351 0.8123 0.562 0.048 Uiso 1 1 calc R
C7 C 0.3338(10) -0.0022(7) 0.1003(5) 0.0553(18) Uani 1 1 d .
H7A H 0.428 -0.005 0.1499 0.083 Uiso 1 1 calc R
H7B H 0.3419 -0.0555 0.0338 0.083 Uiso 1 1 calc R
H7C H 0.2235 -0.0425 0.1325 0.083 Uiso 1 1 calc R
C8 C 0.2067(10) 0.1592(7) -0.0099(5) 0.0536(18) Uani 1 1 d .
H8A H 0.0923 0.1267 0.0193 0.08 Uiso 1 1 calc R
H8B H 0.2153 0.1008 -0.0736 0.08 Uiso 1 1 calc R
H8C H 0.2252 0.2556 -0.0291 0.08 Uiso 1 1 calc R
C16 C 0.0884(11) 1.0061(7) 0.6490(6) 0.063(2) Uani 1 1 d .
H16A H -0.0162 0.9825 0.6902 0.094 Uiso 1 1 calc R
H16B H 0.0695 1.0579 0.5878 0.094 Uiso 1 1 calc R
H16C H 0.1836 1.0632 0.6945 0.094 Uiso 1 1 calc R
C15 C 0.2973(10) 0.8985(11) 0.5405(7) 0.083(3) Uani 1 1 d .
H15A H 0.3964 0.9523 0.5847 0.124 Uiso 1 1 calc R
H15B H 0.2804 0.9514 0.4795 0.124 Uiso 1 1 calc R
H15C H 0.3183 0.8105 0.5147 0.124 Uiso 1 1 calc R
O1 O 0.2762(4) 0.3545(4) 0.1727(3) 0.0283(9) Uani 1 1 d .
O4 O 0.2158(5) 0.6660(4) 0.6845(3) 0.0321(9) Uani 1 1 d .
O3 O 0.0903(5) 0.6500(4) 0.0705(3) 0.0360(10) Uani 1 1 d .
O5 O 0.3999(5) 0.3466(4) 0.5610(3) 0.0380(10) Uani 1 1 d .
O6 O 0.1375(5) 0.3915(4) 0.5761(3) 0.0426(11) Uani 1 1 d .
O2 O 0.3661(5) 0.6324(5) 0.0920(3) 0.0435(11) Uani 1 1 d .
N3 N 0.1681(6) 0.6954(5) 0.8580(3) 0.0322(11) Uani 1 1 d .
N1 N 0.3257(6) 0.3175(5) 0.3436(4) 0.0349(11) Uani 1 1 d .
N2 N 0.3613(6) 0.2087(5) 0.2771(4) 0.0341(11) Uani 1 1 d .
N4 N 0.1254(6) 0.8059(5) 0.8035(4) 0.0340(11) Uani 1 1 d .
H1O H 0.128(6) 0.663(5) -0.015(4) 0.014(11) Uiso 1 1 d .
H2O H 0.380(6) 0.334(5) 0.476(4) 0.014(11) Uiso 1 1 d .
H3 H 0.196(5) 0.528(4) 0.391(4) 0.006(10) Uiso 1 1 d .
H4 H 0.149(7) 0.705(6) 0.277(4) 0.032(14) Uiso 1 1 d .
H11 H 0.308(5) 0.493(4) 0.888(3) 0.004(10) Uiso 1 1 d .
H12 H 0.368(7) 0.337(6) 0.765(4) 0.026(13) 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
N3 C9 O4 114.1(5)
N3 C9 C11 124.3(5)
O4 C9 C11 121.6(5)
N1 C1 O1 112.7(5)
N1 C1 C3 125.9(5)
O1 C1 C3 121.4(4)
N4 C10 O4 111.6(4)
N4 C10 C14 130.6(5)
O4 C10 C14 117.8(5)
O6 C13 O5 123.4(5)
O6 C13 C12 123.8(5)
O5 C13 C12 112.6(4)
O2 C5 O3 123.3(5)
O2 C5 C4 124.1(5)
O3 C5 C4 112.5(4)
C12 C11 C9 127.9(5)
N2 C2 O1 110.7(4)
N2 C2 C6 130.5(5)
O1 C2 C6 118.8(4)
C4 C3 C1 126.3(5)
C3 C4 C5 127.9(5)
C11 C12 C13 128.0(5)
C2 C6 C7 109.3(5)
C2 C6 C8 111.5(5)
C7 C6 C8 111.3(5)
C10 C14 C15 111.1(5)
C10 C14 C16 109.0(5)
C15 C14 C16 112.3(6)
C1 O1 C2 103.0(4)
C9 O4 C10 102.0(4)
C9 N3 N4 105.8(4)
C1 N1 N2 105.8(4)
C2 N2 N1 107.9(4)
C10 N4 N3 106.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 N3 1.278(7)
C9 O4 1.334(6)
C9 C11 1.478(8)
C1 N1 1.287(7)
C1 O1 1.349(6)
C1 C3 1.477(7)
C10 N4 1.273(7)
C10 O4 1.398(6)
C10 C14 1.486(7)
C13 O6 1.224(6)
C13 O5 1.318(6)
C13 C12 1.470(7)
C5 O2 1.223(6)
C5 O3 1.323(6)
C5 C4 1.470(8)
C11 C12 1.336(8)
C2 N2 1.274(7)
C2 O1 1.387(6)
C2 C6 1.481(7)
C3 C4 1.324(8)
C6 C7 1.517(8)
C6 C8 1.532(8)
C14 C15 1.521(9)
C14 C16 1.543(9)
N3 N4 1.411(6)
N1 N2 1.400(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146603
