#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003729.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_2003729
loop_
_publ_author_name
'Wang, X.'
'Wang, W.'
'Liu, H.-X.'
'Tan, M.-Y.'
'Li, M.'
_publ_section_title
;
 A Derivative of 1,3,4-Oxadiazole
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1585
_journal_page_last               1587
_journal_paper_doi               10.1107/S010827019400510X
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        'recrystallization from methanol'
_chemical_formula_moiety         'C13 H9 Cl1 N4 O1'
_chemical_formula_sum            'C13 H9 Cl N4 O'
_chemical_formula_weight         272.70
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 95.86(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   7.080(2)
_cell_length_b                   14.245(1)
_cell_length_c                   12.072(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      24
_cell_measurement_theta_min      12
_cell_volume                     1211.2(5)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1687
_diffrn_reflns_theta_max         55
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.80
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.50
_exptl_crystal_density_meas      1.55
_exptl_crystal_description       cubic
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.88
_refine_ls_hydrogen_treatment
'All H-atom parameters refined with B~iso~ = 4 \%A^2^'
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1416
_refine_ls_R_factor_obs          0.052
_refine_ls_shift/esd_max         0.240
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4(F~o~)^2^/[\s(F~o~)^2^]^2^'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.068
_reflns_number_observed          1416
_reflns_number_total             1610
_reflns_observed_criterion       F>3\s(F)
_cod_data_source_file            ab1133.cif
_cod_data_source_block           ab1133a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '4(F~o~)^2^/[\s(F~o~)^2^]^2^' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
4(F~o~)^2^/[\s(F~o~)^2^]^2^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1211.1(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C13 H9 Cl1 N4 O1'
_cod_database_code               2003729
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
Cl 0.0564(4) 0.0170(3) 0.0178(4) 0.0825(5) -0.0205(4) 0.0830(5)
O 0.0395(8) -0.0024(7) 0.0154(7) 0.0390(8) 0.0013(8) 0.0596(9)
N(1) 0.043(1) -0.0022(9) 0.0219(9) 0.039(1) -0.000(1) 0.070(1)
N(2) 0.045(1) -0.0017(9) 0.023(1) 0.039(1) -0.002(1) 0.076(1)
N(3) 0.048(1) -0.0020(9) 0.020(1) 0.040(1) -0.001(1) 0.074(1)
N(4) 0.047(1) 0.0060(9) 0.010(1) 0.048(1) -0.003(1) 0.057(1)
C(1) 0.043(1) 0.007(1) 0.007(1) 0.059(2) -0.002(1) 0.048(1)
C(2) 0.055(1) 0.005(1) 0.008(1) 0.043(1) -0.005(1) 0.061(1)
C(3) 0.051(1) -0.001(1) 0.009(1) 0.041(1) 0.000(1) 0.056(1)
C(4) 0.040(1) 0.003(1) 0.007(1) 0.041(1) 0.001(1) 0.049(1)
C(5) 0.040(1) 0.001(1) 0.010(1) 0.043(1) 0.002(1) 0.054(1)
C(6) 0.046(1) -0.001(1) 0.011(1) 0.054(1) 0.001(1) 0.056(1)
C(7) 0.037(1) 0.002(1) 0.011(1) 0.043(1) -0.000(1) 0.052(1)
C(8) 0.039(1) -0.001(1) 0.007(1) 0.035(1) 0.002(1) 0.055(1)
C(9) 0.042(1) 0.004(1) 0.004(1) 0.039(1) 0.002(1) 0.046(1)
C(10) 0.045(1) -0.003(1) 0.014(1) 0.038(1) -0.002(1) 0.075(2)
C(11) 0.046(1) 0.001(1) 0.016(1) 0.052(1) -0.002(1) 0.072(2)
C(12) 0.050(1) -0.001(1) 0.007(1) 0.040(1) -0.003(1) 0.054(1)
C(13) 0.043(1) -0.005(1) 0.009(1) 0.045(1) -0.001(1) 0.060(1)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
Cl .21670(9) .37971(5) .62385(6) 5.78(2)
O 1.0275(2) .0828(1) .3501(1) 3.58(3)
N(1) .8476(3) .1960(1) .4234(2) 3.92(4)
N(2) .7629(3) .0333(1) .4153(2) 4.12(5)
N(3) .8566(3) -.0432(1) .3736(2) 4.21(5)
N(4) 1.4120(3) -.1760(1) .1859(2) 3.98(5)
C(1) .4045(3) .3235(2) .5676(2) 3.94(5)
C(2) .5592(4) .3746(2) .5434(2) 4.18(5)
C(3) .7037(3) .3308(2) .4962(2) 3.87(5)
C(4) .6947(3) .2353(2) .4732(2) 3.42(5)
C(5) .5398(3) .1849(2) .5010(2) 3.58(3)
C(6) .3941(3) .2287(2) .5480(2) 4.05(5)
C(7) .8685(3) .1048(2) .3992(2) 3.43(5)
C(8) 1.0081(3) -.0126(2) .3362(2) 3.40(5)
C(9) 1.1499(3) -.0664(2) .2851(2) 3.33(5)
C(10) 1.3163(3) -.0291(2) .2568(2) 4.13(6)
C(11) 1.4418(3) -.0852(2) .2078(2) 4.42(6)
C(12) 1.2507(3) -.2122(2) .2161(2) 3.79(5)
C(13) 1.1173(3) -.1614(2) .2648(2) 3.87(5)
H1N .417(4) .268(2) .894(2) 4.0
H2 .571(4) .439(2) .561(2) 4.0
H3 .813(4) .366(2) .480(2) 4.0
H5 .540(4) .120(2) .491(2) 4.0
H6 .289(4) .189(2) .570(2) 4.0
H10 .350(4) .034(2) .272(2) 4.0
H11 .439(4) .060(2) .813(2) 4.0
H12 .770(3) .276(2) .796(3) 4.0
H13 .489(3) .312(2) .221(2) 4.0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(7) O C(8) 101.8(2) yes
C(4) N(1) C(7) 125.7(3) yes
N(3) N(2) C(7) 105.0(2) yes
N(2) N(3) C(8) 107.9(2) yes
C(11) N(4) C(12) 116.3(3) yes
Cl C(1) C(2) 119.7(2) yes
Cl C(1) C(6) 119.3(2) yes
C(2) C(1) C(6) 121.0(2) yes
C(1) C(2) C(3) 119.6(2) yes
C(2) C(3) C(4) 120.5(2) yes
N(1) C(4) C(3) 116.9(3) yes
N(1) C(4) C(5) 124.3(2) yes
C(3) C(4) C(5) 118.9(2) yes
C(4) C(5) C(6) 120.8(2) yes
C(1) C(6) C(5) 119.2(2) yes
O C(7) N(1) 115.7(2) yes
O C(7) N(2) 113.6(3) yes
N(1) C(7) N(2) 130.8(2) yes
O C(8) N(3) 111.8(3) yes
O C(8) C(9) 120.6(2) yes
N(3) C(8) C(9) 127.6(2) yes
C(8) C(9) C(10) 123.6(2) yes
C(8) C(9) C(13) 118.7(3) yes
C(10) C(9) C(13) 117.8(2) yes
C(9) C(10) C(11) 119.6(2) yes
N(4) C(11) C(10) 123.6(2) yes
N(4) C(12) C(13) 124.0(2) yes
C(9) C(13) C(12) 118.7(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C(1) 1.747(3) yes
O C(7) 1.362(3) yes
O C(8) 1.374(3) yes
N(1) C(4) 1.408(4) yes
N(1) C(7) 1.343(3) yes
N(2) N(3) 1.397(3) yes
N(2) C(7) 1.290(4) yes
N(3) C(8) 1.282(3) yes
N(4) C(11) 1.334(3) yes
N(4) C(12) 1.337(3) yes
C(1) C(2) 1.372(4) yes
C(1) C(6) 1.372(4) yes
C(2) C(3) 1.371(4) yes
C(3) C(4) 1.389(3) yes
C(4) C(5) 1.380(3) yes
C(5) C(6) 1.377(3) yes
C(8) C(9) 1.450(3) yes
C(9) C(10) 1.367(3) yes
C(9) C(13) 1.390(4) yes
C(10) C(11) 1.373(4) yes
C(12) C(13) 1.370(4) yes
N(1) H1N 0.82(3) no
C(2) H2 0.95(3) no
C(3) H3 0.96(3) no
C(5) H5 0.94(3) no
C(6) H6 0.99(3) no
C(10) H10 0.94(3) no
C(11) H11 0.97(3) no
C(12) H12 0.92(3) no
C(13) H13 0.88(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 14044453