#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/95/2229572.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_2229572
loop_
_publ_author_name
'Chernyshev, Victor M.'
'Mazharova, Anna G.'
'Rybakov, Victor B.'
_publ_section_title
;
 4-Benzyl-3-[(1-oxidoethylidene)amino]-1-phenyl-4,5-dihydro-1H-1,2,4-triazol-5-iminium
;
_journal_coeditor_code           AA2002
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o870
_journal_page_last               o871
_journal_paper_doi               10.1107/S1600536811006751
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H17 N5 O'
_chemical_formula_moiety         'C17 H17 N5 O'
_chemical_formula_sum            'C17 H17 N5 O'
_chemical_formula_weight         307.36
_chemical_melting_point_gt       472
_chemical_melting_point_lt       473
_chemical_name_systematic
;
4-Benzyl-3-[(1-oxidoethylidene)amino]-1-phenyl-4,5-dihydro-1H-
1,2,4-triazol-5-iminium
;
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.86(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.262(2)
_cell_length_b                   15.240(3)
_cell_length_c                   10.967(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14.37
_cell_measurement_theta_min      13.15
_cell_volume                     1568.6(6)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56085
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3582
_diffrn_reflns_theta_full        20.97
_diffrn_reflns_theta_max         20.97
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        -1
_diffrn_standards_interval_time  6
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.219
_refine_ls_extinction_coef       0.066(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0590
_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)+(0.0799P)²+0.4611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                2294
_reflns_number_total             3412
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            aa2002.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229572
_cod_database_fobs_code          2229572
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.86753(18) 0.33588(11) 0.43051(16) 0.0345(4) Uani d . 1 . .
N N2 0.96176(18) 0.26764(11) 0.49396(16) 0.0355(4) Uani d . 1 . .
C C3 0.9547(2) 0.21474(13) 0.39830(19) 0.0314(5) Uani d . 1 . .
N N4 0.85963(17) 0.24731(11) 0.27474(15) 0.0314(4) Uani d . 1 . .
C C5 0.8081(2) 0.32385(13) 0.29796(19) 0.0315(5) Uani d . 1 . .
C C6 0.8381(2) 0.21434(14) 0.14185(19) 0.0340(5) Uani d . 1 . .
H H6A 0.7417 0.2280 0.0797 0.041 Uiso calc R 1 . .
H H6B 0.8481 0.1510 0.1459 0.041 Uiso calc R 1 . .
C C7 0.9406(2) 0.25232(14) 0.0901(2) 0.0383(5) Uani d . 1 . .
C C8 1.0832(3) 0.2325(2) 0.1442(3) 0.0597(7) Uani d . 1 . .
H H8 1.1190 0.1948 0.2169 0.072 Uiso calc R 1 . .
C C9 1.1747(3) 0.2673(2) 0.0931(3) 0.0688(8) Uani d . 1 . .
H H9 1.2711 0.2533 0.1322 0.083 Uiso calc R 1 . .
C C10 1.1255(4) 0.3211(2) -0.0126(4) 0.0812(10) Uani d . 1 . .
H H10 1.1868 0.3434 -0.0484 0.097 Uiso calc R 1 . .
C C11 0.9848(5) 0.3428(3) -0.0668(5) 0.128(2) Uani d . 1 . .
H H11 0.9499 0.3807 -0.1395 0.153 Uiso calc R 1 . .
C C12 0.8939(3) 0.3090(3) -0.0146(4) 0.0911(12) Uani d . 1 . .
H H12 0.7983 0.3252 -0.0518 0.109 Uiso calc R 1 . .
N N13 1.04305(18) 0.14482(11) 0.41734(17) 0.0371(4) Uani d . 1 . .
C C14 0.9911(2) 0.06725(14) 0.3633(2) 0.0393(5) Uani d . 1 . .
O O14 0.86200(18) 0.04827(10) 0.30395(16) 0.0492(5) Uani d . 1 . .
C C15 1.1022(3) -0.00100(17) 0.3782(3) 0.0563(7) Uani d . 1 . .
H H15A 1.0685 -0.0575 0.3914 0.084 Uiso calc R 1 . .
H H15B 1.1885 0.0131 0.4536 0.084 Uiso calc R 1 . .
H H15C 1.1207 -0.0022 0.2991 0.084 Uiso calc R 1 . .
C C16 0.8529(2) 0.40728(14) 0.5074(2) 0.0381(5) Uani d . 1 . .
C C17 0.7220(3) 0.44477(17) 0.4786(2) 0.0520(6) Uani d . 1 . .
H H17 0.6411 0.4231 0.4095 0.062 Uiso calc R 1 . .
C C18 0.7124(4) 0.5152(2) 0.5538(3) 0.0678(8) Uani d . 1 . .
H H18 0.6249 0.5424 0.5333 0.081 Uiso calc R 1 . .
C C19 0.8311(5) 0.5452(2) 0.6586(3) 0.0751(10) Uani d . 1 . .
H H19 0.8238 0.5924 0.7092 0.090 Uiso calc R 1 . .
C C20 0.9602(4) 0.50577(19) 0.6889(3) 0.0637(8) Uani d . 1 . .
H H20 1.0397 0.5256 0.7614 0.076 Uiso calc R 1 . .
C C21 0.9741(3) 0.43706(16) 0.6133(2) 0.0474(6) Uani d . 1 . .
H H21 1.0624 0.4112 0.6327 0.057 Uiso calc R 1 . .
N N51 0.7197(2) 0.37631(13) 0.2071(2) 0.0438(5) Uani d . 1 . .
H H51A 0.695(3) 0.433(2) 0.223(2) 0.053(7) Uiso d . 1 . .
H H51B 0.689(3) 0.361(2) 0.127(3) 0.070(9) 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 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 9 -6
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
C5 N4 C3 . . 107.27(16) ?
C5 N4 C6 . . 124.75(16) ?
C3 N4 C6 . . 127.11(17) ?
N51 C5 N1 . . 127.6(2) ?
N51 C5 N4 . . 125.98(19) ?
N1 C5 N4 . . 106.38(16) ?
C5 N1 N2 . . 110.92(16) ?
C5 N1 C16 . . 129.54(17) ?
N2 N1 C16 . . 119.44(16) ?
C3 N2 N1 . . 104.94(15) ?
N2 C3 N13 . . 123.07(17) ?
N2 C3 N4 . . 110.47(17) ?
N13 C3 N4 . . 125.89(18) ?
N4 C6 C7 . . 113.32(17) ?
N4 C6 H6A . . 108.9 ?
C7 C6 H6A . . 108.9 ?
N4 C6 H6B . . 108.9 ?
C7 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.7 ?
C12 C7 C8 . . 117.1(2) ?
C12 C7 C6 . . 120.2(2) ?
C8 C7 C6 . . 122.7(2) ?
C7 C8 C9 . . 121.5(3) ?
C7 C8 H8 . . 119.2 ?
C9 C8 H8 . . 119.2 ?
C10 C9 C8 . . 120.4(3) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 119.3(3) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C12 . . 120.3(3) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C7 C12 C11 . . 121.5(3) ?
C7 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C14 N13 C3 . . 120.35(18) ?
O14 C14 N13 . . 125.8(2) ?
O14 C14 C15 . . 119.6(2) ?
N13 C14 C15 . . 114.6(2) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C21 . . 121.2(2) ?
C17 C16 N1 . . 120.7(2) ?
C21 C16 N1 . . 118.2(2) ?
C16 C17 C18 . . 119.0(3) ?
C16 C17 H17 . . 120.5 ?
C18 C17 H17 . . 120.5 ?
C19 C18 C17 . . 120.3(3) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C20 C19 C18 . . 120.2(3) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C21 . . 120.9(3) ?
C19 C20 H20 . . 119.6 ?
C21 C20 H20 . . 119.6 ?
C20 C21 C16 . . 118.4(3) ?
C20 C21 H21 . . 120.8 ?
C16 C21 H21 . . 120.8 ?
C5 N51 H51A . . 125.1(15) ?
C5 N51 H51B . . 118(2) ?
H51A N51 H51B . . 116(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
N4 C5 . 1.347(3) ?
N4 C3 . 1.402(2) ?
N4 C6 . 1.471(3) ?
C5 N51 . 1.313(3) ?
C5 N1 . 1.342(2) ?
N1 N2 . 1.399(2) ?
N1 C16 . 1.422(3) ?
N2 C3 . 1.302(3) ?
C3 N13 . 1.359(3) ?
C6 C7 . 1.499(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C12 . 1.360(4) ?
C7 C8 . 1.371(3) ?
C8 C9 . 1.379(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.341(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.361(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.378(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
N13 C14 . 1.333(3) ?
C14 O14 . 1.251(3) ?
C14 C15 . 1.503(3) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C17 . 1.374(3) ?
C16 C21 . 1.390(3) ?
C17 C18 . 1.382(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.371(5) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.368(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.378(4) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
N51 H51A . 0.94(3) ?
N51 H51B . 0.84(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
N51 H51A O14 2_655 0.94(3) 1.83(3) 2.739(3) 161(2)
N51 H51B N13 4_565 0.84(3) 2.18(3) 2.971(3) 157(3)
C6 H6B O14 1_555 0.97 2.30 3.045(3) 133
C8 H8 N13 1_555 0.93 2.72 3.454(4) 136
C17 H17 N51 1_555 0.93 2.75 3.146(4) 107
C12 H12 N13 4_565 0.93 2.54 3.441(4) 162
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
C3 N4 C5 N51 . . . . 177.4(2) ?
C6 N4 C5 N51 . . . . 7.4(3) ?
C3 N4 C5 N1 . . . . -1.2(2) ?
C6 N4 C5 N1 . . . . -171.22(18) ?
N51 C5 N1 N2 . . . . -177.0(2) ?
N4 C5 N1 N2 . . . . 1.6(2) ?
N51 C5 N1 C16 . . . . -0.7(4) ?
N4 C5 N1 C16 . . . . 177.9(2) ?
C5 N1 N2 C3 . . . . -1.4(2) ?
C16 N1 N2 C3 . . . . -178.07(18) ?
N1 N2 C3 N13 . . . . 172.37(18) ?
N1 N2 C3 N4 . . . . 0.5(2) ?
C5 N4 C3 N2 . . . . 0.4(2) ?
C6 N4 C3 N2 . . . . 170.09(18) ?
C5 N4 C3 N13 . . . . -171.11(19) ?
C6 N4 C3 N13 . . . . -1.4(3) ?
C5 N4 C6 C7 . . . . 82.4(2) ?
C3 N4 C6 C7 . . . . -85.5(2) ?
N4 C6 C7 C12 . . . . -110.7(3) ?
N4 C6 C7 C8 . . . . 69.3(3) ?
C12 C7 C8 C9 . . . . -1.1(4) ?
C6 C7 C8 C9 . . . . 178.9(2) ?
C7 C8 C9 C10 . . . . -0.7(5) ?
C8 C9 C10 C11 . . . . 1.6(6) ?
C9 C10 C11 C12 . . . . -0.8(7) ?
C8 C7 C12 C11 . . . . 2.0(6) ?
C6 C7 C12 C11 . . . . -178.0(4) ?
C10 C11 C12 C7 . . . . -1.1(8) ?
N2 C3 N13 C14 . . . . 135.3(2) ?
N4 C3 N13 C14 . . . . -54.2(3) ?
C3 N13 C14 O14 . . . . -7.3(3) ?
C3 N13 C14 C15 . . . . 172.8(2) ?
C5 N1 C16 C17 . . . . 42.3(3) ?
N2 N1 C16 C17 . . . . -141.7(2) ?
C5 N1 C16 C21 . . . . -138.6(2) ?
N2 N1 C16 C21 . . . . 37.4(3) ?
C21 C16 C17 C18 . . . . 2.2(4) ?
N1 C16 C17 C18 . . . . -178.7(2) ?
C16 C17 C18 C19 . . . . -2.2(4) ?
C17 C18 C19 C20 . . . . 0.4(5) ?
C18 C19 C20 C21 . . . . 1.5(4) ?
C19 C20 C21 C16 . . . . -1.5(4) ?
C17 C16 C21 C20 . . . . -0.4(3) ?
N1 C16 C21 C20 . . . . -179.5(2) ?
