#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/25/2202506.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_2202506
loop_
_publ_author_name
'Karakurt, Tuncay'
'Dinçer, Muharrem'
'Kahveci, Bahittin'
'Aǧar, Erbil'
'Aǧar, Ayşen'
'Şaşmaz, Selami'
_publ_section_title
;
 1-Benzoyl-3-methyl-4-benzylidenamino-4,5-dihydro-1,2,4-triazol-5-one
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1616
_journal_page_last               o1617
_journal_paper_doi               10.1107/S160053680302110X
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C17 H14 N4 O2'
_chemical_formula_sum            'C17 H14 N4 O2'
_chemical_formula_weight         306.32
_chemical_name_systematic
;
1-Benzoyl-3-methyl-4-benzylidenamino-4,5-dihydro-1,2,4-triazol-5-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGx routine-INITIALIS'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.853(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.850(4)
_cell_length_b                   7.4438(5)
_cell_length_c                   15.3364(19)
_cell_measurement_reflns_used    9403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.37
_cell_measurement_theta_min      2.9
_cell_volume                     3056.9(6)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2001)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1990)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.072
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4262
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.19
_refine_ls_extinction_coef       0.0073(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.87
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.87
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.038
_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)+(0.0712P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                1899
_reflns_number_total             2700
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ci6275.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2202506
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O1 0.09847(4) 0.36780(17) 0.07162(7) 0.0670(3) Uani d . 1 . . O
O2 -0.00443(4) 0.34140(14) -0.06988(7) 0.0534(3) Uani d . 1 . . O
N1 0.02997(4) 0.24251(16) 0.08681(8) 0.0466(3) Uani d . 1 . . N
N2 0.01385(4) 0.13695(16) 0.14525(8) 0.0506(3) Uani d . 1 . . N
N3 -0.04492(4) 0.15810(16) 0.00416(8) 0.0469(3) Uani d . 1 . . N
N4 -0.09291(4) 0.12851(17) -0.06017(9) 0.0522(3) Uani d . 1 . . N
C1 0.09808(5) 0.35066(19) 0.22599(10) 0.0466(3) Uani d . 1 . . C
C2 0.14769(6) 0.3088(2) 0.27716(12) 0.0599(4) Uani d . 1 . . C
C3 0.16684(7) 0.3368(3) 0.37343(13) 0.0742(5) Uani d . 1 . . C
C4 0.13747(7) 0.4088(3) 0.41766(13) 0.0708(5) Uani d . 1 . . C
C5 0.08900(7) 0.4567(2) 0.36665(12) 0.0613(4) Uani d . 1 . . C
C6 0.06926(6) 0.4247(2) 0.27183(11) 0.0524(4) Uani d . 1 . . C
C7 0.07776(5) 0.3244(2) 0.12329(10) 0.0479(3) Uani d . 1 . . C
C8 -0.03103(5) 0.08932(19) 0.09317(10) 0.0479(4) Uani d . 1 . . C
C9 -0.00586(5) 0.25976(19) -0.00324(10) 0.0442(3) Uani d . 1 . . C
C10 -0.06381(7) -0.0257(3) 0.12361(14) 0.0598(4) Uani d . 1 . . C
C11 -0.10455(6) 0.1822(2) -0.14356(11) 0.0533(4) Uani d . 1 . . C
C12 -0.15538(5) 0.1493(2) -0.21097(11) 0.0565(4) Uani d . 1 . . C
C13 -0.19200(6) 0.0743(3) -0.18338(16) 0.0719(5) Uani d . 1 . . C
C14 -0.23885(7) 0.0400(3) -0.2499(2) 0.0943(7) Uani d . 1 . . C
C15 -0.24912(9) 0.0797(4) -0.3414(2) 0.1131(10) Uani d . 1 . . C
C16 -0.21337(10) 0.1538(4) -0.36962(19) 0.1075(8) Uani d . 1 . . C
C17 -0.16628(7) 0.1897(3) -0.30391(14) 0.0746(5) Uani d . 1 . . C
H1 -0.1410(8) 0.240(3) -0.3278(14) 0.092(6) Uiso d . 1 . . H
H2 -0.2195(9) 0.179(4) -0.4345(19) 0.124(9) Uiso d . 1 . . H
H3 -0.2816(12) 0.051(4) -0.389(2) 0.154(10) Uiso d . 1 . . H
H4 -0.2631(10) -0.015(4) -0.2251(16) 0.119(8) Uiso d . 1 . . H
H5 -0.1844(7) 0.044(3) -0.1153(15) 0.085(6) Uiso d . 1 . . H
H6 -0.0814(6) 0.240(2) -0.1661(11) 0.066(5) Uiso d . 1 . . H
H7 -0.0943(9) 0.036(3) 0.1227(16) 0.117(8) Uiso d . 1 . . H
H8 -0.0754(8) -0.126(3) 0.0833(15) 0.096(7) Uiso d . 1 . . H
H9 -0.0466(7) -0.059(3) 0.1895(14) 0.082(6) Uiso d . 1 . . H
H10 0.1675(6) 0.257(2) 0.2427(11) 0.063(4) Uiso d . 1 . . H
H11 0.1998(8) 0.297(3) 0.4046(14) 0.088(6) Uiso d . 1 . . H
H12 0.1511(7) 0.432(3) 0.4887(15) 0.087(6) Uiso d . 1 . . H
H13 0.0697(7) 0.512(3) 0.4041(13) 0.080(5) Uiso d . 1 . . H
H14 0.0351(7) 0.462(2) 0.2336(12) 0.070(5) Uiso d . 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'
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
_geom_angle_publ_flag
C9 N1 N2 112.83(11) ?
C9 N1 C7 127.37(12) yes
N2 N1 C7 119.74(11) yes
C8 N2 N1 104.73(11) ?
C8 N3 N4 119.59(11) yes
C8 N3 C9 109.73(11) ?
N4 N3 C9 130.59(12) yes
C11 N4 N3 119.34(12) yes
C6 C1 C2 119.29(14) ?
C6 C1 C7 121.25(13) ?
C2 C1 C7 119.38(13) ?
C3 C2 C1 119.13(16) ?
C3 C2 H10 123.1(10) ?
C1 C2 H10 117.7(10) ?
C4 C3 C2 120.62(17) ?
C4 C3 H11 124.3(12) ?
C2 C3 H11 114.9(12) ?
C5 C4 C3 120.29(16) ?
C5 C4 H12 118.0(11) ?
C3 C4 H12 121.7(11) ?
C6 C5 C4 119.52(17) ?
C6 C5 H13 124.6(10) ?
C4 C5 H13 115.9(10) ?
C5 C6 C1 121.06(15) ?
C5 C6 H14 120.7(10) ?
C1 C6 H14 118.0(10) ?
O1 C7 N1 120.33(13) yes
O1 C7 C1 124.83(13) yes
N1 C7 C1 114.84(12) yes
N2 C8 N3 111.55(12) ?
N2 C8 C10 125.23(14) yes
N3 C8 C10 123.22(13) yes
O2 C9 N1 130.04(13) yes
O2 C9 N3 128.80(13) yes
N1 C9 N3 101.16(11) ?
C8 C10 H7 113.6(14) ?
C8 C10 H8 111.3(12) ?
H7 C10 H8 105.1(18) ?
C8 C10 H9 109.6(11) ?
H7 C10 H9 103.9(17) ?
H8 C10 H9 113.1(17) ?
N4 C11 C12 118.75(15) yes
N4 C11 H6 123.3(10) ?
C12 C11 H6 117.9(10) ?
C17 C12 C13 119.76(16) ?
C17 C12 C11 118.52(16) ?
C13 C12 C11 121.70(16) ?
C14 C13 C12 119.6(2) ?
C14 C13 H5 119.9(11) ?
C12 C13 H5 120.5(11) ?
C15 C14 C13 120.1(2) ?
C15 C14 H4 124.7(14) ?
C13 C14 H4 115.2(14) ?
C14 C15 C16 120.9(2) ?
C14 C15 H3 120.7(18) ?
C16 C15 H3 118.3(18) ?
C15 C16 C17 119.8(3) ?
C15 C16 H2 122.1(16) ?
C17 C16 H2 118.1(16) ?
C12 C17 C16 119.8(2) ?
C12 C17 H1 122.9(12) ?
C16 C17 H1 117.2(12) ?
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 C7 . 1.2008(17) yes
O2 C9 . 1.2029(17) yes
N1 C9 . 1.3890(18) yes
N1 N2 . 1.3955(16) yes
N1 C7 . 1.4179(18) yes
N2 C8 . 1.2924(17) ?
N3 C8 . 1.3708(18) yes
N3 N4 . 1.3863(16) yes
N3 C9 . 1.3967(18) yes
N4 C11 . 1.260(2) yes
C1 C6 . 1.387(2) ?
C1 C2 . 1.388(2) ?
C1 C7 . 1.475(2) yes
C2 C3 . 1.386(3) ?
C2 H10 . 0.989(18) ?
C3 C4 . 1.376(3) ?
C3 H11 . 0.94(2) ?
C4 C5 . 1.371(3) ?
C4 H12 . 1.03(2) ?
C5 C6 . 1.371(2) ?
C5 H13 . 1.023(19) ?
C6 H14 . 0.983(18) ?
C8 C10 . 1.474(2) yes
C10 H7 . 0.99(3) ?
C10 H8 . 0.95(2) ?
C10 H9 . 0.98(2) ?
C11 C12 . 1.467(2) yes
C11 H6 . 0.963(17) ?
C12 C17 . 1.374(3) ?
C12 C13 . 1.393(2) ?
C13 C14 . 1.381(3) ?
C13 H5 . 1.01(2) ?
C14 C15 . 1.355(4) ?
C14 H4 . 1.00(3) ?
C15 C16 . 1.374(4) ?
C15 H3 . 0.98(3) ?
C16 C17 . 1.383(3) ?
C16 H2 . 0.96(3) ?
C17 H1 . 1.00(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
C11 H6 O2 . 0.96(2) 2.29(2) 2.932(2) 124.0(10)
C5 H13 O1 6_566 1.02(2) 2.55(2) 3.320(2) 132(2)
C5 H13 O2 6_566 1.02(2) 2.56(2) 3.525(2) 157(2)
C17 H1 Cg1 5_565 1.00(2) 2.89(2) 3.537(2) 123(2)
C14 H4 Cg2 4_444 1.00(3) 2.93(3) 3.684(3) 132(2)
C10 H7 Cg1 2_555 0.99(3) 2.87(2) 3.644(2) 136(2)
C2 H10 Cg2 5_555 0.99(2) 2.92(2) 3.527(2) 120.0(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174681
