#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/25/2202549.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_2202549
loop_
_publ_author_name
'Şamil Işık'
'Kahveci, Bahittin'
'Ayşen Ag̃ar'
'Selami Şaşmaz'
_publ_section_title
3-Benzyl-4-(p-fluorobenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1053
_journal_page_last               o1054
_journal_paper_doi               10.1107/S1600536803011474
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C16 H13 F N4 O'
_chemical_formula_moiety         'C16 H13 F N4 O'
_chemical_formula_sum            'C16 H13 F N4 O'
_chemical_formula_weight         296.30
_chemical_name_systematic
;
3-Benzyl-4-(p-Fluorobenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                96.40(2)
_cell_angle_beta                 102.944(17)
_cell_angle_gamma                108.394(16)
_cell_formula_units_Z            2
_cell_length_a                   7.0290(15)
_cell_length_b                   10.141(2)
_cell_length_c                   11.205(3)
_cell_measurement_reflns_used    8077
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.47
_cell_measurement_theta_min      0.00
_cell_volume                     724.2(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.879
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3550
_diffrn_reflns_theta_full        13.01
_diffrn_reflns_theta_max         29.27
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.173
_refine_ls_extinction_coef       0.028(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1093P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                2341
_reflns_number_total             3550
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv6196.cif
_cod_data_source_block           I
_cod_database_code               2202549
_cod_database_fobs_code          2202549
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
F1 -1.4326(2) -0.61860(15) 0.06208(10) 0.1022(4) Uani d . 1 . . F
O1 -1.11115(17) -0.55461(11) 0.82528(10) 0.0617(3) Uani d . 1 . . O
N1 -1.17520(16) -0.36093(13) 0.64075(10) 0.0500(3) Uani d . 1 . . N
N2 -1.0435(2) -0.34595(13) 0.96421(12) 0.0593(3) Uani d . 1 . . N
H2N -1.0214 -0.3758 1.0331 0.088(6) Uiso d R 1 . . H
N3 -1.0307(2) -0.20838(14) 0.95922(12) 0.0590(3) Uani d . 1 . . N
N4 -1.11808(16) -0.33816(12) 0.77025(10) 0.0479(3) Uani d . 1 . . N
C1 -1.3825(2) -0.5857(2) 0.18884(15) 0.0668(5) Uani d . 1 . . C
C2 -1.3695(2) -0.68901(19) 0.25405(17) 0.0682(5) Uani d . 1 . . C
H2 -1.3964 -0.7808 0.2134 0.084(6) Uiso d R 1 . . H
C3 -1.3146(2) -0.65300(17) 0.38293(15) 0.0607(4) Uani d . 1 . . C
H3 -1.3043 -0.7219 0.4297 0.070(5) Uiso d R 1 . . H
C4 -1.27424(19) -0.51637(15) 0.44418(13) 0.0514(3) Uani d . 1 . . C
C5 -1.2921(2) -0.41500(18) 0.37347(14) 0.0608(4) Uani d . 1 . . C
H5 -1.2669 -0.3232 0.4131 0.071(5) Uiso d R 1 . . H
C6 -1.3469(3) -0.4491(2) 0.24488(16) 0.0708(5) Uani d . 1 . . C
H6 -1.3590 -0.3812 0.1971 0.091(7) Uiso d R 1 . . H
C7 -1.2139(2) -0.48508(16) 0.58112(14) 0.0538(3) Uani d . 1 . . C
H7 -1.2039 -0.5565 0.6248 0.068(5) Uiso d R 1 . . H
C8 -1.0934(2) -0.42931(15) 0.85141(13) 0.0512(3) Uani d . 1 . . C
C9 -1.0778(2) -0.20621(15) 0.84086(13) 0.0503(3) Uani d . 1 . . C
C10 -1.0716(2) -0.07868(16) 0.78746(14) 0.0547(3) Uani d . 1 . . C
H10A -1.0914 -0.0099 0.8464 0.068(5) Uiso d R 1 . . H
H10B -1.1848 -0.1042 0.7116 0.049(4) Uiso d R 1 . . H
C11 -0.8661(2) -0.01279(14) 0.75829(13) 0.0500(3) Uani d . 1 . . C
C12 -0.8509(3) -0.02903(18) 0.63691(14) 0.0621(4) Uani d . 1 . . C
H12 -0.9684 -0.0814 0.5718 0.065(5) Uiso d R 1 . . H
C13 -0.6634(3) 0.0318(2) 0.61191(18) 0.0757(5) Uani d . 1 . . C
H13 -0.6551 0.0211 0.5299 0.135(9) Uiso d R 1 . . H
C14 -0.4882(3) 0.1079(2) 0.7073(2) 0.0794(5) Uani d . 1 . . C
H14 -0.3615 0.1491 0.6902 0.094(6) Uiso d R 1 . . H
C15 -0.5010(3) 0.1231(2) 0.8279(2) 0.0845(6) Uani d . 1 . . C
H15 -0.3823 0.1737 0.8929 0.087(6) Uiso d R 1 . . H
C16 -0.6887(3) 0.06387(18) 0.85354(16) 0.0701(5) Uani d . 1 . . C
H16 -0.6960 0.0755 0.9356 0.103(7) Uiso d R 1 . . H
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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C7 N1 N4 117.68(13) yes
C8 N2 N3 113.84(13) ?
C8 N2 H2N 123.1 ?
N3 N2 H2N 123.1 ?
C9 N3 N2 104.55(12) ?
C9 N4 N1 120.65(12) ?
C9 N4 C8 108.21(11) ?
N1 N4 C8 131.14(12) ?
C2 C1 F1 118.45(16) ?
C2 C1 C6 123.13(16) ?
F1 C1 C6 118.41(18) ?
C1 C2 C3 117.67(15) ?
C1 C2 H2 121.2 ?
C3 C2 H2 121.2 ?
C2 C3 C4 121.53(16) ?
C2 C3 H3 119.3 ?
C4 C3 H3 119.2 ?
C5 C4 C3 118.65(14) ?
C5 C4 C7 122.70(13) ?
C3 C4 C7 118.65(15) ?
C6 C5 C4 120.59(15) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C1 C6 C5 118.42(18) ?
C1 C6 H6 120.8 ?
C5 C6 H6 120.8 ?
N1 C7 C4 120.54(15) ?
N1 C7 H7 119.7 ?
C4 C7 H7 119.7 ?
O1 C8 N2 129.27(14) ?
O1 C8 N4 128.10(13) ?
N2 C8 N4 102.63(12) ?
N3 C9 N4 110.75(13) ?
N3 C9 C10 125.16(13) ?
N4 C9 C10 123.88(13) ?
C9 C10 C11 111.28(12) ?
C9 C10 H10A 109.3 ?
C11 C10 H10A 109.3 ?
C9 C10 H10B 109.4 ?
C11 C10 H10B 109.4 ?
H10A C10 H10B 108.0 ?
C16 C11 C12 118.65(14) ?
C16 C11 C10 120.16(14) ?
C12 C11 C10 121.18(13) ?
C13 C12 C11 120.49(16) ?
C13 C12 H12 119.7 ?
C11 C12 H12 119.8 ?
C14 C13 C12 120.32(17) ?
C14 C13 H13 119.9 ?
C12 C13 H13 119.8 ?
C15 C14 C13 119.63(17) ?
C15 C14 H14 120.2 ?
C13 C14 H14 120.2 ?
C14 C15 C16 120.39(17) ?
C14 C15 H15 119.9 ?
C16 C15 H15 119.7 ?
C15 C16 C11 120.51(17) ?
C15 C16 H16 119.7 ?
C11 C16 H16 119.8 ?
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
F1 C1 . 1.3598(19) yes
O1 C8 . 1.2314(18) yes
N1 C7 . 1.2730(19) yes
N1 N4 . 1.3878(16) yes
N2 C8 . 1.3459(19) yes
N2 N3 . 1.3777(19) yes
N2 H2N . 0.8596 ?
N3 C9 . 1.2975(19) yes
N4 C9 . 1.3859(18) yes
N4 C8 . 1.3890(19) yes
C1 C2 . 1.357(3) ?
C1 C6 . 1.376(3) ?
C2 C3 . 1.383(2) ?
C2 H2 . 0.9302 ?
C3 C4 . 1.387(2) ?
C3 H3 . 0.9301 ?
C4 C5 . 1.385(2) ?
C4 C7 . 1.466(2) ?
C5 C6 . 1.379(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9304 ?
C7 H7 . 0.9299 ?
C9 C10 . 1.477(2) ?
C10 C11 . 1.514(2) ?
C10 H10A . 0.9698 ?
C10 H10B . 0.9702 ?
C11 C16 . 1.380(2) ?
C11 C12 . 1.384(2) ?
C12 C13 . 1.374(2) ?
C12 H12 . 0.9294 ?
C13 C14 . 1.372(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.369(3) ?
C14 H14 . 0.9294 ?
C15 C16 . 1.375(3) ?
C15 H15 . 0.9297 ?
C16 H16 . 0.9294 ?
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
N2 H2N O1 2_347 0.86 1.97 2.799(2) 161
C7 H7 O1 . 0.93 2.19 2.893(2) 132
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
C8 N2 N3 C9 1.31(16)
C7 N1 N4 C9 -178.74(12)
C7 N1 N4 C8 0.14(19)
F1 C1 C2 C3 178.80(13)
C6 C1 C2 C3 -1.0(3)
C1 C2 C3 C4 0.1(2)
C2 C3 C4 C5 0.7(2)
C2 C3 C4 C7 -179.16(13)
C3 C4 C5 C6 -0.6(2)
C7 C4 C5 C6 179.21(14)
C2 C1 C6 C5 1.1(3)
F1 C1 C6 C5 -178.73(14)
C4 C5 C6 C1 -0.2(2)
N4 N1 C7 C4 -179.74(10)
C5 C4 C7 N1 0.0(2)
C3 C4 C7 N1 179.86(12)
N3 N2 C8 O1 177.93(13)
N3 N2 C8 N4 -1.39(15)
C9 N4 C8 O1 -178.40(13)
N1 N4 C8 O1 2.6(2)
C9 N4 C8 N2 0.94(14)
N1 N4 C8 N2 -178.05(12)
N2 N3 C9 N4 -0.62(15)
N2 N3 C9 C10 -175.56(13)
N1 N4 C9 N3 178.91(10)
C8 N4 C9 N3 -0.20(15)
N1 N4 C9 C10 -6.07(19)
C8 N4 C9 C10 174.82(12)
N3 C9 C10 C11 94.75(16)
N4 C9 C10 C11 -79.54(16)
C9 C10 C11 C16 -75.33(18)
C9 C10 C11 C12 103.94(17)
C16 C11 C12 C13 -0.9(3)
C10 C11 C12 C13 179.82(16)
C11 C12 C13 C14 0.8(3)
C12 C13 C14 C15 0.0(3)
C13 C14 C15 C16 -0.7(3)
C14 C15 C16 C11 0.6(3)
C12 C11 C16 C15 0.2(3)
C10 C11 C16 C15 179.48(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654711
