##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
data_1t
_audit_creation_method     'SHELXL-2016/6'
_chemical_name_systematic
;
3-Cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H11 N5 O'
_chemical_formula_sum     'C10 H11 N5 O'
_chemical_formula_iupac     'C10 H11 N5 O'
_chemical_formula_weight     217.24
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.4476(10)
_cell_length_b     8.5662(8)
_cell_length_c     8.6125(8)
_cell_angle_alpha     110.812(9)
_cell_angle_beta     115.048(11)
_cell_angle_gamma     92.854(9)
_cell_volume     512.82(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     846
_cell_measurement_theta_min     4.207
_cell_measurement_theta_max     25.738
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.200
_exptl_crystal_size_mid     0.170
_exptl_crystal_size_min     0.100
_exptl_crystal_density_diffrn     1.407
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     228
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_absorpt_correction_T_min     0.18773
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Rigaku Xcalibur Sapphire3'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.1827
_diffrn_reflns_number     3563
_diffrn_reflns_av_R_equivalents     0.0427
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_theta_min     3.312
_diffrn_reflns_theta_max     25.000
_diffrn_reflns_theta_full     25.000
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     9
_refine_special_details     ?
_reflns_number_total     1795
_reflns_number_gt     1337
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0679
_refine_ls_R_factor_gt     0.0529
_refine_ls_wR_factor_gt     0.1455
_refine_ls_wR_factor_ref     0.1637
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_restrained_S_all     1.056
_refine_ls_number_reflns     1795
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0858P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.203
_refine_diff_density_min     -0.211
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
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 0.6672(2) 0.56003(19) 0.9056(2) 0.0672(5) Uani d 1 . .
    N N1 0.8289(3) 0.6863(3) 0.9853(3) 0.0741(6) Uani d 1 . .
    N N2 0.7711(2) 0.4883(2) 0.7013(2) 0.0554(5) Uani d 1 . .
    N N3 0.3083(2) 0.0515(2) 0.3385(3) 0.0597(5) Uani d 1 . .
    N N4 0.5318(3) 0.2269(2) 0.3501(3) 0.0604(5) Uani d 1 . .
    H H4 0.637(4) 0.302(3) 0.409(4) 0.086(8) Uiso d 1 . .
    N N5 0.4945(3) 0.1157(3) 0.1664(3) 0.0686(6) Uani d 1 . .
    H H5NA 0.479(4) 0.005(4) 0.162(4) 0.106(10) Uiso d 1 . .
    H H5NB 0.382(4) 0.125(3) 0.088(4) 0.089(9) Uiso d 1 . .
    C C1 0.6453(3) 0.4486(3) 0.7380(3) 0.0521(5) Uani d 1 . .
    C C2 0.8817(3) 0.6343(3) 0.8581(3) 0.0612(6) Uani d 1 . .
    C C3 1.0478(3) 0.7243(3) 0.8816(3) 0.0697(7) Uani d 1 . .
    H H3 1.115238 0.830316 0.996389 0.084 Uiso calc 1 . .
    C C4 1.0535(3) 0.7184(3) 0.7084(4) 0.0739(7) Uani d 1 . .
    H H4A 0.946671 0.655610 0.588201 0.089 Uiso calc 1 . .
    H H4B 1.120473 0.819869 0.718224 0.089 Uiso calc 1 . .
    C C5 1.1560(3) 0.6188(3) 0.8065(4) 0.0762(7) Uani d 1 . .
    H H5A 1.285910 0.659122 0.876536 0.091 Uiso calc 1 . .
    H H5B 1.112103 0.494859 0.746510 0.091 Uiso calc 1 . .
    C C6 0.4923(3) 0.3020(2) 0.6283(3) 0.0515(5) Uani d 1 . .
    C C7 0.3911(3) 0.2607(3) 0.7049(3) 0.0583(6) Uani d 1 . .
    H H7 0.416969 0.330972 0.827516 0.070 Uiso calc 1 . .
    C C8 0.2524(3) 0.1164(3) 0.6011(3) 0.0632(6) Uani d 1 . .
    H H8 0.183345 0.087335 0.651314 0.076 Uiso calc 1 . .
    C C9 0.2187(3) 0.0162(3) 0.4206(4) 0.0656(6) Uani d 1 . .
    H H9 0.126635 -0.083141 0.351538 0.079 Uiso calc 1 . .
    C C10 0.4442(3) 0.1922(3) 0.4374(3) 0.0507(5) Uani d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C1 . 1.344(2) ?
    O1 N1 . 1.428(2) ?
    N1 C2 . 1.299(3) ?
    N2 C1 . 1.293(3) ?
    N2 C2 . 1.369(3) ?
    N3 C9 . 1.322(3) ?
    N3 C10 . 1.342(3) ?
    N4 C10 . 1.344(3) ?
    N4 N5 . 1.410(3) ?
    N4 H4 . 0.89(3) ?
    N5 H5NA . 0.94(3) ?
    N5 H5NB . 0.93(3) ?
    C1 C6 . 1.449(3) ?
    C2 C3 . 1.465(3) ?
    C3 C4 . 1.495(3) ?
    C3 C5 . 1.496(4) ?
    C3 H3 . 0.9800 ?
    C4 C5 . 1.469(3) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.381(3) ?
    C6 C10 . 1.432(3) ?
    C7 C8 . 1.372(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.373(3) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
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
    C1 O1 N1 . . 105.88(15) ?
    C2 N1 O1 . . 102.95(18) ?
    C1 N2 C2 . . 103.20(17) ?
    C9 N3 C10 . . 118.7(2) ?
    C10 N4 N5 . . 122.60(18) ?
    C10 N4 H4 . . 124.1(18) ?
    N5 N4 H4 . . 111.1(18) ?
    N4 N5 H5NA . . 105.2(19) ?
    N4 N5 H5NB . . 105.1(17) ?
    H5NA N5 H5NB . . 106(3) ?
    N2 C1 O1 . . 113.07(18) ?
    N2 C1 C6 . . 129.37(18) ?
    O1 C1 C6 . . 117.54(17) ?
    N1 C2 N2 . . 114.88(19) ?
    N1 C2 C3 . . 122.4(2) ?
    N2 C2 C3 . . 122.7(2) ?
    C2 C3 C4 . . 117.8(2) ?
    C2 C3 C5 . . 118.1(2) ?
    C4 C3 C5 . . 58.81(16) ?
    C2 C3 H3 . . 116.6 ?
    C4 C3 H3 . . 116.6 ?
    C5 C3 H3 . . 116.6 ?
    C5 C4 C3 . . 60.61(17) ?
    C5 C4 H4A . . 117.7 ?
    C3 C4 H4A . . 117.7 ?
    C5 C4 H4B . . 117.7 ?
    C3 C4 H4B . . 117.7 ?
    H4A C4 H4B . . 114.8 ?
    C4 C5 C3 . . 60.58(16) ?
    C4 C5 H5A . . 117.7 ?
    C3 C5 H5A . . 117.7 ?
    C4 C5 H5B . . 117.7 ?
    C3 C5 H5B . . 117.7 ?
    H5A C5 H5B . . 114.8 ?
    C7 C6 C10 . . 117.7(2) ?
    C7 C6 C1 . . 121.45(19) ?
    C10 C6 C1 . . 120.79(18) ?
    C8 C7 C6 . . 120.3(2) ?
    C8 C7 H7 . . 119.8 ?
    C6 C7 H7 . . 119.8 ?
    C7 C8 C9 . . 117.93(18) ?
    C7 C8 H8 . . 121.0 ?
    C9 C8 H8 . . 121.0 ?
    N3 C9 C8 . . 124.3(2) ?
    N3 C9 H9 . . 117.8 ?
    C8 C9 H9 . . 117.8 ?
    N3 C10 N4 . . 117.64(19) ?
    N3 C10 C6 . . 120.90(18) ?
    N4 C10 C6 . . 121.46(19) ?
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
    C1 O1 N1 C2 . . . . -0.3(2) ?
    C2 N2 C1 O1 . . . . 0.8(2) ?
    C2 N2 C1 C6 . . . . -177.3(2) ?
    N1 O1 C1 N2 . . . . -0.3(2) ?
    N1 O1 C1 C6 . . . . 177.99(17) ?
    O1 N1 C2 N2 . . . . 0.9(3) ?
    O1 N1 C2 C3 . . . . -178.65(19) ?
    C1 N2 C2 N1 . . . . -1.1(3) ?
    C1 N2 C2 C3 . . . . 178.5(2) ?
    N1 C2 C3 C4 . . . . -149.0(2) ?
    N2 C2 C3 C4 . . . . 31.5(3) ?
    N1 C2 C3 C5 . . . . 143.4(3) ?
    N2 C2 C3 C5 . . . . -36.1(3) ?
    C2 C3 C4 C5 . . . . -107.6(3) ?
    C2 C3 C5 C4 . . . . 107.2(2) ?
    N2 C1 C6 C7 . . . . 166.7(2) ?
    O1 C1 C6 C7 . . . . -11.2(3) ?
    N2 C1 C6 C10 . . . . -11.5(3) ?
    O1 C1 C6 C10 . . . . 170.48(17) ?
    C10 C6 C7 C8 . . . . 1.6(3) ?
    C1 C6 C7 C8 . . . . -176.74(18) ?
    C6 C7 C8 C9 . . . . 0.0(3) ?
    C10 N3 C9 C8 . . . . 1.5(4) ?
    C7 C8 C9 N3 . . . . -1.6(4) ?
    C9 N3 C10 N4 . . . . -179.08(19) ?
    C9 N3 C10 C6 . . . . 0.3(3) ?
    N5 N4 C10 N3 . . . . -4.6(3) ?
    N5 N4 C10 C6 . . . . 176.1(2) ?
    C7 C6 C10 N3 . . . . -1.8(3) ?
    C1 C6 C10 N3 . . . . 176.59(18) ?
    C7 C6 C10 N4 . . . . 177.56(19) ?
    C1 C6 C10 N4 . . . . -4.1(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N4 H4 N2 . 0.89(3) 2.17(3) 2.795(3) 127(2)
    N5 H5NA C8 2_656 0.94(3) 2.87(3) 3.487(3) 125(2)
    N5 H5NB N1 2_666 0.93(3) 2.50(3) 3.325(4) 148(2)
    N5 H5NA N3 . 0.94(3) 2.45(3) 2.728(2) 97(2)
_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     0.990
data_1r
_audit_creation_method     'SHELXL-2016/6'
_chemical_name_systematic
;
3-Cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H11 N5 O'
_chemical_formula_sum     'C10 H11 N5 O'
_chemical_formula_iupac     'C10 H11 N5 O'
_chemical_formula_weight     217.24
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
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'
_cell_length_a     4.8240(11)
_cell_length_b     8.2685(19)
_cell_length_c     26.527(10)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1058.1(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     655
_cell_measurement_theta_min     3.947
_cell_measurement_theta_max     20.041
_cell_measurement_temperature     293(2)
_exptl_crystal_description     stick
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.200
_exptl_crystal_size_mid     0.050
_exptl_crystal_size_min     0.050
_exptl_crystal_density_diffrn     1.364
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     456
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_absorpt_correction_T_min     0.17551
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Rigaku Xcalibur Sapphire3'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.1827
_diffrn_reflns_number     7941
_diffrn_reflns_av_R_equivalents     0.0804
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_theta_min     3.373
_diffrn_reflns_theta_max     24.995
_diffrn_reflns_theta_full     24.995
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -31
_diffrn_reflns_limit_l_max     31
_refine_special_details     ?
_reflns_number_total     1859
_reflns_number_gt     1194
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0909
_refine_ls_R_factor_gt     0.0512
_refine_ls_wR_factor_gt     0.0997
_refine_ls_wR_factor_ref     0.1194
_refine_ls_goodness_of_fit_ref     0.990
_refine_ls_restrained_S_all     0.990
_refine_ls_number_reflns     1859
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0373P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.137
_refine_diff_density_min     -0.130
_refine_ls_extinction_method
;
SHELXL2016 (Sheldrick, 2015b)
;
_refine_ls_extinction_coef     0.007(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
Flack x determined using 320 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     -0.7(10)
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'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
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 0.3081(6) 0.5574(4) 0.66612(13) 0.0744(10) Uani d 1 . .
    N N1 0.1474(7) 0.6666(5) 0.69605(17) 0.0774(11) Uani d 1 . .
    N N2 0.4560(6) 0.8019(4) 0.64848(14) 0.0577(9) Uani d 1 . .
    N N3 1.0284(7) 0.5842(4) 0.54210(14) 0.0650(10) Uani d 1 . .
    N N4 0.8594(7) 0.8191(4) 0.57554(15) 0.0627(10) Uani d 1 . .
    H H4N 0.733(8) 0.878(5) 0.6013(18) 0.078(14) Uiso d 1 . .
    N N5 1.0260(11) 0.9131(5) 0.5430(2) 0.0726(12) Uani d 1 . .
    H H5NA 1.190(10) 0.871(6) 0.5497(18) 0.082(18) Uiso d 1 . .
    H H5NB 0.960(10) 0.900(6) 0.514(2) 0.10(2) Uiso d 1 . .
    C C1 0.4820(8) 0.6484(5) 0.63948(16) 0.0568(11) Uani d 1 . .
    C C2 0.2470(7) 0.8070(6) 0.68382(18) 0.0630(12) Uani d 1 . .
    C C3 0.1501(8) 0.9554(6) 0.70658(19) 0.0690(13) Uani d 1 . .
    H H3 0.003885 0.944058 0.731985 0.083 Uiso calc 1 . .
    C C4 0.1412(10) 1.1041(6) 0.6759(2) 0.0820(15) Uani d 1 . .
    H H4A 0.201476 1.096713 0.641069 0.098 Uiso calc 1 . .
    H H4B -0.010220 1.178923 0.681769 0.098 Uiso calc 1 . .
    C C5 0.3504(9) 1.0890(6) 0.7148(2) 0.0913(18) Uani d 1 . .
    H H5A 0.328856 1.154211 0.744962 0.110 Uiso calc 1 . .
    H H5B 0.540637 1.071967 0.704246 0.110 Uiso calc 1 . .
    C C6 0.6711(8) 0.5670(5) 0.60523(17) 0.0530(11) Uani d 1 . .
    C C7 0.6770(9) 0.4014(5) 0.6022(2) 0.0677(13) Uani d 1 . .
    H H7 0.558548 0.339649 0.622056 0.081 Uiso calc 1 . .
    C C8 0.8581(10) 0.3271(6) 0.5697(2) 0.0782(15) Uani d 1 . .
    H H8 0.866570 0.214969 0.567491 0.094 Uiso calc 1 . .
    C C9 1.0241(10) 0.4218(6) 0.5411(2) 0.0744(14) Uani d 1 . .
    H H9 1.144768 0.370362 0.518949 0.089 Uiso calc 1 . .
    C C10 0.8517(8) 0.6557(5) 0.57396(17) 0.0541(11) Uani d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C1 . 1.330(5) ?
    O1 N1 . 1.431(5) ?
    N1 C2 . 1.297(5) ?
    N2 C1 . 1.298(5) ?
    N2 C2 . 1.377(5) ?
    N3 C10 . 1.338(5) ?
    N3 C9 . 1.343(5) ?
    N4 C10 . 1.352(5) ?
    N4 N5 . 1.413(5) ?
    N4 H4N . 1.04(4) ?
    N5 H5NA . 0.88(5) ?
    N5 H5NB . 0.84(5) ?
    C1 C6 . 1.453(6) ?
    C2 C3 . 1.445(6) ?
    C3 C4 . 1.475(6) ?
    C3 C5 . 1.484(6) ?
    C3 H3 . 0.9800 ?
    C4 C5 . 1.449(7) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.372(5) ?
    C6 C10 . 1.409(6) ?
    C7 C8 . 1.371(6) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.354(6) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
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
    C1 O1 N1 . . 106.2(3) ?
    C2 N1 O1 . . 103.0(3) ?
    C1 N2 C2 . . 103.0(4) ?
    C10 N3 C9 . . 116.4(4) ?
    C10 N4 N5 . . 123.1(4) ?
    C10 N4 H4N . . 118(2) ?
    N5 N4 H4N . . 119(2) ?
    N4 N5 H5NA . . 100(3) ?
    N4 N5 H5NB . . 106(4) ?
    H5NA N5 H5NB . . 118(5) ?
    N2 C1 O1 . . 113.3(4) ?
    N2 C1 C6 . . 129.0(4) ?
    O1 C1 C6 . . 117.8(4) ?
    N1 C2 N2 . . 114.5(4) ?
    N1 C2 C3 . . 122.4(4) ?
    N2 C2 C3 . . 123.2(4) ?
    C2 C3 C4 . . 119.1(4) ?
    C2 C3 C5 . . 118.9(4) ?
    C4 C3 C5 . . 58.6(3) ?
    C2 C3 H3 . . 116.0 ?
    C4 C3 H3 . . 116.0 ?
    C5 C3 H3 . . 116.0 ?
    C5 C4 C3 . . 61.0(3) ?
    C5 C4 H4A . . 117.7 ?
    C3 C4 H4A . . 117.7 ?
    C5 C4 H4B . . 117.7 ?
    C3 C4 H4B . . 117.7 ?
    H4A C4 H4B . . 114.8 ?
    C4 C5 C3 . . 60.4(3) ?
    C4 C5 H5A . . 117.7 ?
    C3 C5 H5A . . 117.7 ?
    C4 C5 H5B . . 117.7 ?
    C3 C5 H5B . . 117.7 ?
    H5A C5 H5B . . 114.9 ?
    C7 C6 C10 . . 118.2(4) ?
    C7 C6 C1 . . 120.8(4) ?
    C10 C6 C1 . . 121.0(4) ?
    C8 C7 C6 . . 119.8(5) ?
    C8 C7 H7 . . 120.1 ?
    C6 C7 H7 . . 120.1 ?
    C9 C8 C7 . . 118.0(4) ?
    C9 C8 H8 . . 121.0 ?
    C7 C8 H8 . . 121.0 ?
    N3 C9 C8 . . 125.2(5) ?
    N3 C9 H9 . . 117.4 ?
    C8 C9 H9 . . 117.4 ?
    N3 C10 N4 . . 116.4(4) ?
    N3 C10 C6 . . 122.4(4) ?
    N4 C10 C6 . . 121.3(4) ?
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
    C1 O1 N1 C2 . . . . -0.5(4) ?
    C2 N2 C1 O1 . . . . -0.1(5) ?
    C2 N2 C1 C6 . . . . -180.0(4) ?
    N1 O1 C1 N2 . . . . 0.4(5) ?
    N1 O1 C1 C6 . . . . -179.7(3) ?
    O1 N1 C2 N2 . . . . 0.5(5) ?
    O1 N1 C2 C3 . . . . -178.0(4) ?
    C1 N2 C2 N1 . . . . -0.3(5) ?
    C1 N2 C2 C3 . . . . 178.2(4) ?
    N1 C2 C3 C4 . . . . -146.1(5) ?
    N2 C2 C3 C4 . . . . 35.5(6) ?
    N1 C2 C3 C5 . . . . 145.8(5) ?
    N2 C2 C3 C5 . . . . -32.5(7) ?
    C2 C3 C4 C5 . . . . -107.9(5) ?
    C2 C3 C5 C4 . . . . 108.3(5) ?
    N2 C1 C6 C7 . . . . 177.2(4) ?
    O1 C1 C6 C7 . . . . -2.6(6) ?
    N2 C1 C6 C10 . . . . -3.3(7) ?
    O1 C1 C6 C10 . . . . 176.8(4) ?
    C10 C6 C7 C8 . . . . 0.8(7) ?
    C1 C6 C7 C8 . . . . -179.7(4) ?
    C6 C7 C8 C9 . . . . -0.8(7) ?
    C10 N3 C9 C8 . . . . -0.5(7) ?
    C7 C8 C9 N3 . . . . 0.7(8) ?
    C9 N3 C10 N4 . . . . 179.0(4) ?
    C9 N3 C10 C6 . . . . 0.4(6) ?
    N5 N4 C10 N3 . . . . 5.0(7) ?
    N5 N4 C10 C6 . . . . -176.4(4) ?
    C7 C6 C10 N3 . . . . -0.6(6) ?
    C1 C6 C10 N3 . . . . 179.9(4) ?
    C7 C6 C10 N4 . . . . -179.1(4) ?
    C1 C6 C10 N4 . . . . 1.4(6) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N4 H4N N2 . 1.04(4) 1.93(4) 2.748(5) 133(3)
    N5 H5NB N3 4_466 0.84(5) 2.56(5) 3.295(7) 146(5)
    N5 H5NA N3 . 0.88(5) 2.51(5) 2.720(6) 94(3)
_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
data_global
_journal_date_recd_electronic     2020-06-10
_journal_date_accepted     2020-07-28
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2020
_journal_volume     76
_journal_issue      8
_journal_page_first     836
_journal_page_last     844
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229620010414
_journal_coeditor_code     KU3265
_publ_contact_author_name     'Svitlana V. Shishkina'
_publ_contact_author_address
;
SSI `Institute for Single Crystals' NAS of Ukraine
60 Nauky ave.
Kharkiv 61001
Ukraine
V.N. Karazin Kharkiv National University
4 Svobody sq.
Kharkiv 61077
Ukraine
;
_publ_contact_author_email     sveta@xray.isc.kharkov.com
_publ_section_title
;
Concomitant polymorphic forms of
3-cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Svitlana V. Shishkina' .
;
SSI `Institute for Single Crystals' NAS of Ukraine
60 Nauky ave.
Kharkiv 61001
Ukraine
V.N. Karazin Kharkiv National University
4 Svobody sq.
Kharkiv 61077
Ukraine
;
    'Irina S. Konovalova' .
;
SSI `Institute for Single Crystals' NAS of Ukraine
60 Nauky ave.
Kharkiv 61001
Ukraine
;
    'Veronika R. Karpina' .
;
National University of Pharmacy
53 Pushkinska str.
Kharkiv 61002
Ukraine
;
    'Svitlana S. Kovalenko' .
;
National University of Pharmacy
53 Pushkinska str.
Kharkiv 61002
Ukraine
;
    'Sergiy M. Kovalenko' .
;
V.N. Karazin Kharkiv National University
4 Svobody sq.
Kharkiv 61077
Ukraine
Federal State Autonomous Educational Institution of Higher Education
I.M. Sechenov First Moscow State Medical University
8 Trubeckaya
Moscow 119991
Russian Federation
;
    'Natalya D. Bunyatyan' .
;\
Federal State Autonomous Educational Institution of Higher Education
I.M. Sechenov First Moscow State Medical University
8 Trubeckaya
Moscow 119991
Russian Federation
Federal State Budgetary Institution `Scientific Centre for Expert \
Evaluation of Medicinal Products'
Petrovsky boulevard 8
bld. 2
Moscow 127051
Russian Federation
;
_publ_section_synopsis
;
The dipharmacophore compound
3-cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole has been
synthesized and two concomitant polymorphs have been thoroughly studied. The
application of classical and periodic quantum chemical calculations identified
a difference in the crystal packing, which is classified as an isotropic
packing of dimers in the triclinic form and as a columnar packing of molecules
in the orthorhombic form.
;
