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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228274.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_2228274
loop_
_publ_author_name
'Chernyshev, V. M.'
'Astakhov, A. V.'
'Ivanov, V. V.'
'Starikova, Z. A.'
_publ_section_title
;
 N³-[(E)-Morpholin-4-ylmethylidene]-1-phenyl-1H-1,2,4-triazole-3,5-diamine
 monohydrate
;
_journal_coeditor_code           CV2798
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3247
_journal_page_last               o3248
_journal_paper_doi               10.1107/S160053681004729X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H16 N6 O, H2 O'
_chemical_formula_moiety         'C13 H16 N6 O, H2 O'
_chemical_formula_sum            'C13 H18 N6 O2'
_chemical_formula_weight         290.33
_chemical_melting_point          208
_chemical_name_systematic
;
N³-[(E)-Morpholin-4-ylmethylidene]-1-phenyl-1H-1,2,4-
triazole-3,5-diamine monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.9380(10)
_cell_angle_beta                 105.9330(10)
_cell_angle_gamma                95.3310(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7886(7)
_cell_length_b                   9.0100(7)
_cell_length_c                   9.4373(7)
_cell_measurement_reflns_used    334
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     700.00(9)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5231
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0447P)²+0.3407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                2510
_reflns_number_total             2724
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2798.cif
_cod_data_source_block           I
_cod_database_code               2228274
_cod_database_fobs_code          2228274
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.71171(11) 0.75346(9) 0.92066(9) 0.0197(2) Uani d . 1 . .
N N1 0.75642(11) 0.22365(11) 0.11933(11) 0.0140(2) Uani d . 1 . .
N N2 0.73939(12) 0.36780(11) 0.19018(11) 0.0149(2) Uani d . 1 . .
N N4 0.82835(11) 0.22141(11) 0.36142(11) 0.0140(2) Uani d . 1 . .
N N5 0.83821(12) -0.00456(11) 0.19122(12) 0.0163(2) Uani d . 1 . .
H H5A 0.7927(19) -0.0581(18) 0.0975(19) 0.025(4) Uiso d . 1 . .
H H5B 0.8474(19) -0.0575(18) 0.2638(19) 0.027(4) Uiso d . 1 . .
N N3 0.77750(11) 0.48235(11) 0.44096(11) 0.0146(2) Uani d . 1 . .
N N6 0.79432(12) 0.56639(11) 0.69189(11) 0.0154(2) Uani d . 1 . .
C C5 0.80778(13) 0.13965(13) 0.22417(12) 0.0132(2) Uani d . 1 . .
C C3 0.78422(13) 0.35886(13) 0.33343(13) 0.0131(2) Uani d . 1 . .
C C1 0.81153(13) 0.46393(13) 0.57891(13) 0.0139(2) Uani d . 1 . .
H H1 0.8498 0.3750 0.6003 0.017 Uiso calc R 1 . .
C C6 0.85744(15) 0.55214(13) 0.84809(13) 0.0179(3) Uani d . 1 . .
H H6A 0.9620 0.6136 0.8926 0.021 Uiso calc R 1 . .
H H6B 0.8697 0.4468 0.8515 0.021 Uiso calc R 1 . .
C C7 0.74577(17) 0.60386(14) 0.93772(14) 0.0225(3) Uani d . 1 . .
H H7A 0.6468 0.5329 0.9031 0.027 Uiso calc R 1 . .
H H7B 0.7949 0.6046 1.0433 0.027 Uiso calc R 1 . .
C C8 0.63106(14) 0.74989(14) 0.76612(13) 0.0173(2) Uani d . 1 . .
H H8A 0.5986 0.8484 0.7557 0.021 Uiso calc R 1 . .
H H8B 0.5356 0.6743 0.7322 0.021 Uiso calc R 1 . .
C C9 0.73945(15) 0.71137(13) 0.66976(13) 0.0179(3) Uani d . 1 . .
H H9A 0.6819 0.7038 0.5646 0.021 Uiso calc R 1 . .
H H9B 0.8306 0.7912 0.6975 0.021 Uiso calc R 1 . .
C C10 0.71449(14) 0.18521(13) -0.04071(12) 0.0141(2) Uani d . 1 . .
C C11 0.56426(14) 0.20692(14) -0.12420(13) 0.0179(3) Uani d . 1 . .
H H11 0.4903 0.2391 -0.0761 0.021 Uiso calc R 1 . .
C C12 0.52581(15) 0.18009(14) -0.27987(14) 0.0206(3) Uani d . 1 . .
H H12 0.4252 0.1937 -0.3365 0.025 Uiso calc R 1 . .
C C13 0.63660(15) 0.13300(14) -0.35193(13) 0.0188(3) Uani d . 1 . .
H H13 0.6114 0.1180 -0.4562 0.023 Uiso calc R 1 . .
C C14 0.78489(14) 0.10853(13) -0.26786(13) 0.0167(2) Uani d . 1 . .
H H14 0.8581 0.0749 -0.3162 0.020 Uiso calc R 1 . .
C C15 0.82470(14) 0.13401(13) -0.11178(13) 0.0154(2) Uani d . 1 . .
H H15 0.9239 0.1170 -0.0555 0.019 Uiso calc R 1 . .
O O2 0.88944(11) 0.77890(11) 0.38883(10) 0.0217(2) Uani d . 1 . .
H H2A 0.840(2) 0.688(2) 0.389(2) 0.041(5) Uiso d . 1 . .
H H2B 0.979(2) 0.788(2) 0.467(2) 0.048(5) Uiso d . 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
C8 O1 C7 . . 109.34(9) ?
C5 N1 N2 . . 109.50(9) ?
C5 N1 C10 . . 130.86(10) ?
N2 N1 C10 . . 119.58(9) ?
C3 N2 N1 . . 101.95(9) ?
C5 N4 C3 . . 103.04(9) ?
C5 N5 H5A . . 117.9(10) ?
C5 N5 H5B . . 116.4(10) ?
H5A N5 H5B . . 115.6(14) ?
C1 N3 C3 . . 116.52(10) ?
C1 N6 C6 . . 121.12(10) ?
C1 N6 C9 . . 122.19(10) ?
C6 N6 C9 . . 115.74(9) ?
N4 C5 N5 . . 126.03(10) ?
N4 C5 N1 . . 110.18(10) ?
N5 C5 N1 . . 123.76(10) ?
N2 C3 N4 . . 115.33(10) ?
N2 C3 N3 . . 118.89(10) ?
N4 C3 N3 . . 125.73(10) ?
N3 C1 N6 . . 123.28(11) ?
N3 C1 H1 . . 118.4 ?
N6 C1 H1 . . 118.4 ?
N6 C6 C7 . . 110.52(10) ?
N6 C6 H6A . . 109.5 ?
C7 C6 H6A . . 109.5 ?
N6 C6 H6B . . 109.5 ?
C7 C6 H6B . . 109.5 ?
H6A C6 H6B . . 108.1 ?
O1 C7 C6 . . 110.56(10) ?
O1 C7 H7A . . 109.5 ?
C6 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.1 ?
O1 C8 C9 . . 110.45(9) ?
O1 C8 H8A . . 109.6 ?
C9 C8 H8A . . 109.6 ?
O1 C8 H8B . . 109.6 ?
C9 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
N6 C9 C8 . . 109.22(9) ?
N6 C9 H9A . . 109.8 ?
C8 C9 H9A . . 109.8 ?
N6 C9 H9B . . 109.8 ?
C8 C9 H9B . . 109.8 ?
H9A C9 H9B . . 108.3 ?
C11 C10 C15 . . 120.75(10) ?
C11 C10 N1 . . 118.68(10) ?
C15 C10 N1 . . 120.49(10) ?
C12 C11 C10 . . 119.35(11) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C13 . . 120.41(11) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 119.80(11) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C13 C14 C15 . . 120.40(11) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C10 . . 119.25(11) ?
C14 C15 H15 . . 120.4 ?
C10 C15 H15 . . 120.4 ?
H2A O2 H2B . . 101.2(16) ?
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 C8 . 1.4292(14) ?
O1 C7 . 1.4338(15) ?
N1 C5 . 1.3536(15) ?
N1 N2 . 1.3956(13) ?
N1 C10 . 1.4238(14) ?
N2 C3 . 1.3193(15) ?
N4 C5 . 1.3305(15) ?
N4 C3 . 1.3783(15) ?
N5 C5 . 1.3517(15) ?
N5 H5A . 0.893(17) ?
N5 H5B . 0.890(17) ?
N3 C1 . 1.2968(15) ?
N3 C3 . 1.3880(15) ?
N6 C1 . 1.3367(15) ?
N6 C6 . 1.4584(14) ?
N6 C9 . 1.4623(15) ?
C1 H1 . 0.9300 ?
C6 C7 . 1.5167(17) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.5109(16) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.3900(16) ?
C10 C15 . 1.3906(16) ?
C11 C12 . 1.3858(17) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.3897(18) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.3866(17) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.3893(16) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
O2 H2A . 0.89(2) ?
O2 H2B . 0.91(2) ?
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
N5 H5A O1 1_544 0.89(2) 2.08(2) 2.929(2) 159.0(10)
N5 H5B O2 1_545 0.89(2) 2.04(2) 2.906(2) 164.0(10)
O2 H2A N3 1_555 0.89(2) 2.07(2) 2.929(2) 164.0(10)
O2 H2B N4 2_766 0.91(2) 2.01(2) 2.916(2) 172.0(10)
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
C5 N1 N2 C3 . . . . 0.70(11) ?
C10 N1 N2 C3 . . . . 178.22(9) ?
C3 N4 C5 N5 . . . . 178.66(11) ?
C3 N4 C5 N1 . . . . 0.87(12) ?
N2 N1 C5 N4 . . . . -1.03(12) ?
C10 N1 C5 N4 . . . . -178.18(10) ?
N2 N1 C5 N5 . . . . -178.89(10) ?
C10 N1 C5 N5 . . . . 3.96(19) ?
N1 N2 C3 N4 . . . . -0.16(12) ?
N1 N2 C3 N3 . . . . -177.65(9) ?
C5 N4 C3 N2 . . . . -0.43(12) ?
C5 N4 C3 N3 . . . . 176.86(10) ?
C1 N3 C3 N2 . . . . 175.10(10) ?
C1 N3 C3 N4 . . . . -2.11(16) ?
C3 N3 C1 N6 . . . . -172.89(10) ?
C6 N6 C1 N3 . . . . -170.20(11) ?
C9 N6 C1 N3 . . . . -1.83(17) ?
C1 N6 C6 C7 . . . . -143.44(11) ?
C9 N6 C6 C7 . . . . 47.47(14) ?
C8 O1 C7 C6 . . . . 62.51(13) ?
N6 C6 C7 O1 . . . . -52.83(13) ?
C7 O1 C8 C9 . . . . -64.75(12) ?
C1 N6 C9 C8 . . . . 142.14(11) ?
C6 N6 C9 C8 . . . . -48.90(13) ?
O1 C8 C9 N6 . . . . 56.40(13) ?
C5 N1 C10 C11 . . . . 124.87(13) ?
N2 N1 C10 C11 . . . . -52.04(14) ?
C5 N1 C10 C15 . . . . -58.21(16) ?
N2 N1 C10 C15 . . . . 124.87(11) ?
C15 C10 C11 C12 . . . . -1.36(18) ?
N1 C10 C11 C12 . . . . 175.55(10) ?
C10 C11 C12 C13 . . . . -0.46(18) ?
C11 C12 C13 C14 . . . . 1.84(18) ?
C12 C13 C14 C15 . . . . -1.42(18) ?
C13 C14 C15 C10 . . . . -0.37(17) ?
C11 C10 C15 C14 . . . . 1.77(17) ?
N1 C10 C15 C14 . . . . -175.08(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231130
2 PubChem 139080065
