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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/4/50/81/4508153.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_4508153
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 H12 N2 O3'
_chemical_formula_weight         184.2
_space_group_IT_number           61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-08-14T17:20:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8937(6)
_cell_length_b                   10.9771(8)
_cell_length_c                   17.1409(11)
_cell_measurement_temperature    173(2)
_cell_volume                     1861.6(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7045
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0228P)²+0.5405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                1385
_reflns_number_total             1903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400649h_si_002.cif
_cod_data_source_block           gut112
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4508153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
C1 C 0.23390(15) 0.86783(14) 0.33562(9) 0.0218(4) Uani 1 1 d
C3 C 0.35214(17) 0.93802(17) 0.30808(10) 0.0255(4) Uani 1 1 d
C5 C 0.20876(15) 1.08724(14) 0.23418(10) 0.0224(4) Uani 1 1 d
C4 C 0.32524(17) 0.99947(17) 0.23026(10) 0.0247(4) Uani 1 1 d
C2 C 0.10994(16) 0.77229(14) 0.41750(10) 0.0243(4) Uani 1 1 d
C6 C 0.06635(18) 0.72366(17) 0.49436(10) 0.0328(4) Uani 1 1 d
C8 C 0.0420(2) 0.8274(2) 0.55139(13) 0.0464(6) Uani 1 1 d
C7 C 0.1665(3) 0.6316(2) 0.52637(14) 0.0504(6) Uani 1 1 d
N2 N 0.04893(13) 0.76862(12) 0.35158(8) 0.0259(3) Uani 1 1 d
N1 N 0.12999(13) 0.83190(12) 0.29730(8) 0.0259(3) Uani 1 1 d
O2 O 0.15785(11) 1.12319(10) 0.29379(7) 0.0304(3) Uani 1 1 d
O1 O 0.22905(10) 0.83436(10) 0.41240(6) 0.0247(3) Uani 1 1 d
O3 O 0.16825(12) 1.12125(12) 0.16377(7) 0.0336(3) Uani 1 1 d
H3O H 0.098(2) 1.175(2) 0.1667(12) 0.068(7) Uiso 1 1 d
H3 H 0.4059(17) 1.0466(15) 0.2145(9) 0.028(4) Uiso 1 1 d
H1 H 0.4259(16) 0.8815(15) 0.3032(9) 0.026(4) Uiso 1 1 d
H4 H 0.3065(15) 0.9388(16) 0.1913(9) 0.025(4) Uiso 1 1 d
H2 H 0.3732(16) 0.9989(16) 0.3485(9) 0.028(4) Uiso 1 1 d
H5 H -0.0194(17) 0.6837(16) 0.4837(9) 0.032(5) Uiso 1 1 d
H10 H 0.128(2) 0.8705(17) 0.5610(10) 0.042(5) Uiso 1 1 d
H11 H -0.026(2) 0.885(2) 0.5297(12) 0.060(7) Uiso 1 1 d
H8 H 0.130(2) 0.602(2) 0.5737(14) 0.069(7) Uiso 1 1 d
H6 H 0.185(2) 0.567(2) 0.4916(15) 0.085(9) Uiso 1 1 d
H9 H 0.006(2) 0.796(2) 0.6003(13) 0.064(7) Uiso 1 1 d
H7 H 0.255(2) 0.675(2) 0.5416(11) 0.059(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
N1 C1 O1 112.48(13)
N1 C1 C3 129.14(15)
O1 C1 C3 118.38(13)
C1 C3 C4 111.93(14)
O2 C5 O3 123.58(15)
O2 C5 C4 124.60(15)
O3 C5 C4 111.82(14)
C5 C4 C3 112.32(14)
N2 C2 O1 111.47(14)
N2 C2 C6 129.33(15)
O1 C2 C6 119.16(14)
C2 C6 C7 111.73(16)
C2 C6 C8 110.31(17)
C7 C6 C8 111.69(19)
C2 N2 N1 107.34(12)
C1 N1 N2 105.62(13)
C2 O1 C1 103.08(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.2821(19)
C1 O1 1.3672(18)
C1 C3 1.478(2)
C3 C4 1.518(2)
C5 O2 1.2056(18)
C5 O3 1.3253(19)
C5 C4 1.504(2)
C2 N2 1.2817(19)
C2 O1 1.3640(18)
C2 C6 1.485(2)
C6 C7 1.518(3)
C6 C8 1.520(3)
N2 N1 1.4112(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 28284414
