#------------------------------------------------------------------------------
#$Date: 2021-09-29 05:18:57 +0300 (Wed, 29 Sep 2021) $
#$Revision: 269362 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243928.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_2243928
loop_
_publ_author_name
'Pokhodylo, Nazariy T.'
'Slyvka, Yurii'
'Pavlyuk, Volodymyr'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 5-cyclopropyl-N-(2-hydroxyethyl)-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxamide
;
_journal_coeditor_code           HB7983
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021009774
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C15 H18 N4 O2'
_chemical_formula_moiety         'C15 H18 N4 O2'
_chemical_formula_sum            'C15 H18 N4 O2'
_chemical_formula_weight         286.33
_chemical_name_systematic
5-Cyclopropyl-N-(2-hydroxyethyl)-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.040(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3158(6)
_cell_length_b                   8.3972(3)
_cell_length_c                   13.0871(4)
_cell_measurement_reflns_used    1679
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.85
_cell_volume                     1495.90(10)
_computing_cell_refinement
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur3 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8400
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.850
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2004)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lamina
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0468
_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)+(0.0350P)²+0.1800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                1621
_reflns_number_total             2632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7983sup1.cif
_cod_data_source_block           I
_cod_database_code               2243928
_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   0.958
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.13456(11) 0.3294(2) 0.60427(12) 0.0974(5) Uani d 1 . .
O O2 0.06831(14) 0.3928(2) 0.21808(14) 0.1042(6) Uani d 1 . .
H H2 0.092(2) 0.318(4) 0.177(3) 0.171(14) Uiso d 1 . .
N N1 0.44653(12) 0.35154(18) 0.67420(11) 0.0570(4) Uani d 1 . .
N N2 0.43955(13) 0.3492(2) 0.56776(12) 0.0687(5) Uani d 1 . .
N N3 0.34622(13) 0.3512(2) 0.51377(12) 0.0680(5) Uani d 1 . .
N N4 0.14491(15) 0.3789(3) 0.44072(15) 0.0846(6) Uani d 1 . .
H H4 0.1840(16) 0.397(3) 0.4005(17) 0.090(7) Uiso d 1 . .
C C1 0.54283(14) 0.3518(2) 0.75104(14) 0.0573(5) Uani d 1 . .
C C2 0.56125(17) 0.2755(2) 0.84840(16) 0.0660(6) Uani d 1 . .
H H2A 0.510965 0.223701 0.866145 0.079 Uiso calc 1 . .
C C3 0.65554(19) 0.2771(3) 0.91933(17) 0.0755(6) Uani d 1 . .
H H3 0.667851 0.226965 0.985570 0.091 Uiso calc 1 . .
C C4 0.73224(17) 0.3510(3) 0.89461(18) 0.0754(6) Uani d 1 . .
C C5 0.71121(17) 0.4244(3) 0.79535(19) 0.0768(6) Uani d 1 . .
H H5 0.761557 0.474207 0.776551 0.092 Uiso calc 1 . .
C C6 0.61784(16) 0.4254(2) 0.72389(17) 0.0658(5) Uani d 1 . .
H H6 0.605361 0.475465 0.657611 0.079 Uiso calc 1 . .
C C7 0.83533(18) 0.3513(4) 0.9729(2) 0.1156(10) Uani d 1 . .
H H7A 0.853395 0.457928 0.997559 0.173 Uiso calc 1 . .
H H7B 0.880342 0.311663 0.937725 0.173 Uiso calc 1 . .
H H7C 0.837630 0.284323 1.033110 0.173 Uiso calc 1 . .
C C8 0.35570(14) 0.3551(2) 0.68719(14) 0.0546(5) Uani d 1 . .
C C9 0.29293(14) 0.3532(2) 0.58406(14) 0.0583(5) Uani d 1 . .
C C10 0.18463(16) 0.3519(2) 0.54485(16) 0.0671(5) Uani d 1 . .
C C11 0.33673(14) 0.3634(2) 0.79130(14) 0.0616(5) Uani d 1 . .
H H11 0.329955 0.260032 0.823068 0.074 Uiso calc 1 . .
C C12 0.27363(19) 0.4924(3) 0.81202(17) 0.0882(7) Uani d 1 . .
H H12A 0.249069 0.572020 0.756496 0.106 Uiso calc 1 . .
H H12B 0.228996 0.465129 0.851979 0.106 Uiso calc 1 . .
C C13 0.37951(19) 0.4924(3) 0.87037(17) 0.0791(7) Uani d 1 . .
H H13A 0.399859 0.464995 0.946092 0.095 Uiso calc 1 . .
H H13B 0.419936 0.571906 0.850592 0.095 Uiso calc 1 . .
C C14 0.03984(18) 0.3804(3) 0.38523(18) 0.0979(8) Uani d 1 . .
H H14A 0.016031 0.489258 0.378087 0.117 Uiso calc 1 . .
H H14B 0.005972 0.321759 0.427025 0.117 Uiso calc 1 . .
C C15 0.01844(17) 0.3080(3) 0.27817(18) 0.0946(8) Uani d 1 . .
H H15A 0.039484 0.197635 0.285111 0.114 Uiso calc 1 . .
H H15B -0.051722 0.310769 0.241585 0.114 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
C15 O2 H2 . . 108(2) ?
N2 N1 C1 . . 117.80(15) ?
C8 N1 N2 . . 110.87(15) ?
C8 N1 C1 . . 131.32(15) ?
N3 N2 N1 . . 106.95(14) ?
N2 N3 C9 . . 109.13(15) ?
C10 N4 H4 . . 119.3(14) ?
C10 N4 C14 . . 124.32(19) ?
C14 N4 H4 . . 116.4(14) ?
C2 C1 N1 . . 121.04(18) ?
C2 C1 C6 . . 120.41(19) ?
C6 C1 N1 . . 118.51(17) ?
C1 C2 H2A . . 120.5 ?
C1 C2 C3 . . 119.0(2) ?
C3 C2 H2A . . 120.5 ?
C2 C3 H3 . . 119.1 ?
C2 C3 C4 . . 121.9(2) ?
C4 C3 H3 . . 119.1 ?
C3 C4 C7 . . 121.3(2) ?
C5 C4 C3 . . 117.5(2) ?
C5 C4 C7 . . 121.2(2) ?
C4 C5 H5 . . 119.2 ?
C6 C5 C4 . . 121.7(2) ?
C6 C5 H5 . . 119.2 ?
C1 C6 H6 . . 120.2 ?
C5 C6 C1 . . 119.6(2) ?
C5 C6 H6 . . 120.2 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7B . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 C9 . . 103.70(15) ?
N1 C8 C11 . . 124.99(17) ?
C9 C8 C11 . . 131.29(17) ?
N3 C9 C8 . . 109.33(17) ?
N3 C9 C10 . . 120.82(17) ?
C8 C9 C10 . . 129.85(16) ?
O1 C10 N4 . . 122.1(2) ?
O1 C10 C9 . . 122.64(19) ?
N4 C10 C9 . . 115.29(17) ?
C8 C11 H11 . . 115.0 ?
C8 C11 C12 . . 119.99(17) ?
C8 C11 C13 . . 121.51(16) ?
C12 C11 H11 . . 115.0 ?
C12 C11 C13 . . 59.16(14) ?
C13 C11 H11 . . 115.0 ?
C11 C12 H12A . . 117.7 ?
C11 C12 H12B . . 117.7 ?
H12A C12 H12B . . 114.8 ?
C13 C12 C11 . . 60.56(14) ?
C13 C12 H12A . . 117.7 ?
C13 C12 H12B . . 117.7 ?
C11 C13 H13A . . 117.7 ?
C11 C13 H13B . . 117.7 ?
C12 C13 C11 . . 60.28(14) ?
C12 C13 H13A . . 117.7 ?
C12 C13 H13B . . 117.7 ?
H13A C13 H13B . . 114.9 ?
N4 C14 H14A . . 109.5 ?
N4 C14 H14B . . 109.5 ?
N4 C14 C15 . . 110.52(19) ?
H14A C14 H14B . . 108.1 ?
C15 C14 H14A . . 109.5 ?
C15 C14 H14B . . 109.5 ?
O2 C15 C14 . . 109.4(2) ?
O2 C15 H15A . . 109.8 ?
O2 C15 H15B . . 109.8 ?
C14 C15 H15A . . 109.8 ?
C14 C15 H15B . . 109.8 ?
H15A C15 H15B . . 108.3 ?
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 C10 . 1.224(2) ?
O2 H2 . 0.95(3) ?
O2 C15 . 1.408(3) ?
N1 N2 . 1.3655(19) ?
N1 C1 . 1.433(2) ?
N1 C8 . 1.363(2) ?
N2 N3 . 1.304(2) ?
N3 C9 . 1.365(2) ?
N4 H4 . 0.89(2) ?
N4 C10 . 1.324(3) ?
N4 C14 . 1.454(3) ?
C1 C2 . 1.377(3) ?
C1 C6 . 1.378(3) ?
C2 H2A . 0.9300 ?
C2 C3 . 1.381(3) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.384(3) ?
C4 C5 . 1.384(3) ?
C4 C7 . 1.514(3) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.374(3) ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.370(2) ?
C8 C11 . 1.471(2) ?
C9 C10 . 1.475(3) ?
C11 H11 . 0.9800 ?
C11 C12 . 1.488(3) ?
C11 C13 . 1.492(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C12 C13 . 1.471(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 C15 . 1.470(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
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
_geom_hbond_publ_flag
O2 H2 O1 4_565 0.95(3) 1.78(3) 2.734(2) 177(3) yes
C11 H11 N3 4_566 0.98 2.61 3.391(2) 137.1 yes
C5 H5 O2 3_666 0.93 2.66 3.564(3) 163.7 yes
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
N1 N2 N3 C9 . . . . -0.6(2) ?
N1 C1 C2 C3 . . . . 179.09(16) ?
N1 C1 C6 C5 . . . . -178.65(17) ?
N1 C8 C9 N3 . . . . -1.0(2) ?
N1 C8 C9 C10 . . . . 178.57(19) ?
N1 C8 C11 C12 . . . . 125.2(2) ?
N1 C8 C11 C13 . . . . 55.1(3) ?
N2 N1 C1 C2 . . . . -146.14(17) ?
N2 N1 C1 C6 . . . . 31.5(2) ?
N2 N1 C8 C9 . . . . 0.61(19) ?
N2 N1 C8 C11 . . . . -177.98(16) ?
N2 N3 C9 C8 . . . . 1.0(2) ?
N2 N3 C9 C10 . . . . -178.57(17) ?
N3 C9 C10 O1 . . . . 168.7(2) ?
N3 C9 C10 N4 . . . . -12.2(3) ?
N4 C14 C15 O2 . . . . -58.8(3) ?
C1 N1 N2 N3 . . . . -179.30(16) ?
C1 N1 C8 C9 . . . . 179.77(18) ?
C1 N1 C8 C11 . . . . 1.2(3) ?
C1 C2 C3 C4 . . . . -1.0(3) ?
C2 C1 C6 C5 . . . . -1.0(3) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C2 C3 C4 C7 . . . . -179.8(2) ?
C3 C4 C5 C6 . . . . 0.5(3) ?
C4 C5 C6 C1 . . . . 0.0(3) ?
C6 C1 C2 C3 . . . . 1.5(3) ?
C7 C4 C5 C6 . . . . -179.7(2) ?
C8 N1 N2 N3 . . . . 0.0(2) ?
C8 N1 C1 C2 . . . . 34.7(3) ?
C8 N1 C1 C6 . . . . -147.61(19) ?
C8 C9 C10 O1 . . . . -10.8(3) ?
C8 C9 C10 N4 . . . . 168.3(2) ?
C8 C11 C12 C13 . . . . -111.0(2) ?
C8 C11 C13 C12 . . . . 108.5(2) ?
C9 C8 C11 C12 . . . . -53.0(3) ?
C9 C8 C11 C13 . . . . -123.1(2) ?
C10 N4 C14 C15 . . . . -141.9(2) ?
C11 C8 C9 N3 . . . . 177.49(18) ?
C11 C8 C9 C10 . . . . -3.0(3) ?
C14 N4 C10 O1 . . . . -1.9(3) ?
C14 N4 C10 C9 . . . . 179.0(2) ?

_cod_database_fobs_code 2243928
