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#$Date: 2021-02-05 16:53:54 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022293.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_2022293
loop_
_publ_author_name
'Shishkina, Svitlana V.'
'Konovalova, Irina S.'
'Kovalenko, Svitlana S.'
'Nikolaeva, Lyudmila L.'
'Bunyatyan, Natalya D.'
'Kovalenko, Sergiy M.'
_publ_section_title
;
 Conformational polymorphs of
 3-cyclopropyl-5-(3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-1,2,4-oxadiazole
;
_journal_coeditor_code           QF3045
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              20
_journal_page_last               28
_journal_paper_doi               10.1107/S2053229620015508
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C12 H11 N5 O'
_chemical_formula_sum            'C12 H11 N5 O'
_chemical_formula_weight         241.26
_chemical_name_systematic
3-Cyclopropyl-5-(3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-1,2,4-oxadiazole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2191(13)
_cell_length_b                   8.1593(9)
_cell_length_c                   22.788(2)
_cell_measurement_reflns_used    1390
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.033
_cell_measurement_theta_min      3.951
_cell_volume                     2271.9(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15782
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         3.132
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       stick
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0721P)²+0.0520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1583
_reflns_number_gt                1311
_reflns_number_total             2002
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qf3045sup1.cif
_cod_data_source_block           1r
_cod_depositor_comments
'Adding full bibliography for 2022292--2022293.cif.'
_cod_database_code               2022293
_cod_database_fobs_code          2022293
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.88986(12) 0.5205(2) 0.52200(8) 0.0715(5) Uani d 1 . .
N N3 0.80711(15) 0.2052(2) 0.70333(9) 0.0606(5) Uani d 1 . .
N N4 0.71113(15) 0.5058(2) 0.51527(9) 0.0617(6) Uani d 1 . .
N N5 0.86045(17) 0.6039(2) 0.46946(10) 0.0726(6) Uani d 1 . .
N N1 0.62777(18) 0.1981(3) 0.71423(11) 0.0839(7) Uani d 1 . .
N N2 0.6767(2) 0.1183(3) 0.76098(11) 0.0848(7) Uani d 1 . .
C C7 0.79654(18) 0.4670(3) 0.54524(11) 0.0573(6) Uani d 1 . .
C C4 0.80063(17) 0.3756(3) 0.60016(10) 0.0566(6) Uani d 1 . .
C C8 0.75456(19) 0.5904(3) 0.46866(11) 0.0601(6) Uani d 1 . .
C C2 0.90468(18) 0.2421(3) 0.67606(11) 0.0648(7) Uani d 1 . .
H H2 0.971001 0.209978 0.692458 0.078 Uiso calc 1 . .
C C3 0.90181(18) 0.3253(3) 0.62528(11) 0.0638(7) Uani d 1 . .
H H3 0.966972 0.350475 0.606212 0.077 Uiso calc 1 . .
C C6 0.70786(19) 0.2498(3) 0.67980(12) 0.0638(7) Uani d 1 . .
C C5 0.70492(18) 0.3374(3) 0.62699(11) 0.0624(7) Uani d 1 . .
H H5 0.638458 0.368828 0.610597 0.075 Uiso calc 1 . .
C C9 0.68851(19) 0.6572(3) 0.42135(11) 0.0670(7) Uani d 1 . .
H H9 0.727228 0.725505 0.392691 0.080 Uiso calc 1 . .
C C1 0.7831(2) 0.1236(3) 0.75449(12) 0.0699(7) Uani d 1 . .
C C11 0.5717(2) 0.7022(3) 0.43306(12) 0.0756(8) Uani d 1 . .
H H11A 0.544027 0.685885 0.472521 0.091 Uiso calc 1 . .
H H11B 0.542301 0.797114 0.412884 0.091 Uiso calc 1 . .
C C10 0.5957(2) 0.5555(3) 0.39780(12) 0.0797(8) Uani d 1 . .
H H10A 0.581175 0.560604 0.355993 0.096 Uiso calc 1 . .
H H10B 0.582901 0.449340 0.415649 0.096 Uiso calc 1 . .
C C12 0.8657(2) 0.0530(3) 0.79399(12) 0.0854(8) Uani d 1 . .
H H12A 0.904585 -0.032585 0.773953 0.128 Uiso calc 1 . .
H H12B 0.830322 0.008629 0.828076 0.128 Uiso calc 1 . .
H H12C 0.916277 0.136905 0.805742 0.128 Uiso calc 1 . .
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 0.0000 0.0000 '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 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 N5 . . 105.98(17) ?
C1 N3 C6 . . 105.7(2) ?
C1 N3 C2 . . 132.3(2) ?
C6 N3 C2 . . 122.0(2) ?
C7 N4 C8 . . 102.8(2) ?
C8 N5 O1 . . 102.86(18) ?
C6 N1 N2 . . 106.7(2) ?
C1 N2 N1 . . 109.1(2) ?
N4 C7 O1 . . 113.7(2) ?
N4 C7 C4 . . 127.5(2) ?
O1 C7 C4 . . 118.7(2) ?
C5 C4 C3 . . 120.1(2) ?
C5 C4 C7 . . 118.4(2) ?
C3 C4 C7 . . 121.5(2) ?
N5 C8 N4 . . 114.7(2) ?
N5 C8 C9 . . 122.1(2) ?
N4 C8 C9 . . 123.2(2) ?
C3 C2 N3 . . 118.5(2) ?
C3 C2 H2 . . 120.8 ?
N3 C2 H2 . . 120.8 ?
C2 C3 C4 . . 121.0(2) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
N1 C6 N3 . . 109.7(2) ?
N1 C6 C5 . . 130.8(2) ?
N3 C6 C5 . . 119.5(2) ?
C4 C5 C6 . . 118.9(2) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C8 C9 C11 . . 119.3(2) ?
C8 C9 C10 . . 118.4(2) ?
C11 C9 C10 . . 58.70(16) ?
C8 C9 H9 . . 116.1 ?
C11 C9 H9 . . 116.1 ?
C10 C9 H9 . . 116.1 ?
N2 C1 N3 . . 108.9(2) ?
N2 C1 C12 . . 126.9(3) ?
N3 C1 C12 . . 124.2(2) ?
C10 C11 C9 . . 60.88(17) ?
C10 C11 H11A . . 117.7 ?
C9 C11 H11A . . 117.7 ?
C10 C11 H11B . . 117.7 ?
C9 C11 H11B . . 117.7 ?
H11A C11 H11B . . 114.8 ?
C11 C10 C9 . . 60.42(16) ?
C11 C10 H10A . . 117.7 ?
C9 C10 H10A . . 117.7 ?
C11 C10 H10B . . 117.7 ?
C9 C10 H10B . . 117.7 ?
H10A C10 H10B . . 114.8 ?
C1 C12 H12A . . 109.5 ?
C1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.331(3) ?
O1 N5 . 1.423(3) ?
N3 C1 . 1.375(3) ?
N3 C6 . 1.375(3) ?
N3 C2 . 1.378(3) ?
N4 C7 . 1.287(3) ?
N4 C8 . 1.373(3) ?
N5 C8 . 1.299(3) ?
N1 C6 . 1.323(3) ?
N1 N2 . 1.384(3) ?
N2 C1 . 1.309(3) ?
C7 C4 . 1.457(3) ?
C4 C5 . 1.356(3) ?
C4 C3 . 1.423(3) ?
C8 C9 . 1.453(3) ?
C2 C3 . 1.342(3) ?
C2 H2 . 0.9300 ?
C3 H3 . 0.9300 ?
C6 C5 . 1.400(3) ?
C5 H5 . 0.9300 ?
C9 C11 . 1.497(3) ?
C9 C10 . 1.504(3) ?
C9 H9 . 0.9800 ?
C1 C12 . 1.470(4) ?
C11 C10 . 1.471(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 O1 N5 C8 . . . . 0.5(2) ?
C6 N1 N2 C1 . . . . 0.4(3) ?
C8 N4 C7 O1 . . . . 0.5(2) ?
C8 N4 C7 C4 . . . . 179.8(2) ?
N5 O1 C7 N4 . . . . -0.7(2) ?
N5 O1 C7 C4 . . . . 180.00(17) ?
N4 C7 C4 C5 . . . . -6.5(3) ?
O1 C7 C4 C5 . . . . 172.71(19) ?
N4 C7 C4 C3 . . . . 172.8(2) ?
O1 C7 C4 C3 . . . . -8.0(3) ?
O1 N5 C8 N4 . . . . -0.2(2) ?
O1 N5 C8 C9 . . . . -179.14(19) ?
C7 N4 C8 N5 . . . . -0.1(2) ?
C7 N4 C8 C9 . . . . 178.7(2) ?
C1 N3 C2 C3 . . . . -180.0(2) ?
C6 N3 C2 C3 . . . . 0.6(3) ?
N3 C2 C3 C4 . . . . 0.4(3) ?
C5 C4 C3 C2 . . . . -1.1(3) ?
C7 C4 C3 C2 . . . . 179.6(2) ?
N2 N1 C6 N3 . . . . -0.1(3) ?
N2 N1 C6 C5 . . . . -179.7(2) ?
C1 N3 C6 N1 . . . . -0.2(3) ?
C2 N3 C6 N1 . . . . 179.29(19) ?
C1 N3 C6 C5 . . . . 179.48(19) ?
C2 N3 C6 C5 . . . . -1.0(3) ?
C3 C4 C5 C6 . . . . 0.7(3) ?
C7 C4 C5 C6 . . . . -179.95(19) ?
N1 C6 C5 C4 . . . . 179.9(2) ?
N3 C6 C5 C4 . . . . 0.3(3) ?
N5 C8 C9 C11 . . . . -154.4(2) ?
N4 C8 C9 C11 . . . . 26.8(3) ?
N5 C8 C9 C10 . . . . 137.6(2) ?
N4 C8 C9 C10 . . . . -41.2(3) ?
N1 N2 C1 N3 . . . . -0.5(3) ?
N1 N2 C1 C12 . . . . -179.7(2) ?
C6 N3 C1 N2 . . . . 0.5(3) ?
C2 N3 C1 N2 . . . . -179.0(2) ?
C6 N3 C1 C12 . . . . 179.6(2) ?
C2 N3 C1 C12 . . . . 0.2(4) ?
C8 C9 C11 C10 . . . . -107.3(3) ?
C8 C9 C10 C11 . . . . 108.8(3) ?
