#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/19/2201959.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_2201959
loop_
_publ_author_name
'Çoruh, Ufuk'
'Kahveci, Bahittin'
'Şaşmaz, Selami'
'Ag̃ar, Erbil'
'Youngme Kim'
_publ_section_title
1-Acetyl-4-(p-chlorobenzylideneamino)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o530
_journal_page_last               o532
_journal_paper_doi               10.1107/S1600536803005129
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C12 H11 Cl N4 O2'
_chemical_formula_moiety         'C12 H11 Cl N4 O2'
_chemical_formula_sum            'C12 H11 Cl N4 O2'
_chemical_formula_weight         278.70
_chemical_name_systematic
;
1-Acetyl-3-methyl-4-(P-chlorobenzylidenamino)-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                93.13(2)
_cell_angle_beta                 98.20(2)
_cell_angle_gamma                95.86(2)
_cell_formula_units_Z            2
_cell_length_a                   6.910(3)
_cell_length_b                   7.5682(10)
_cell_length_c                   12.380(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.38
_cell_measurement_theta_min      8.21
_cell_volume                     635.9(3)
_computing_cell_refinement       'CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-7 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 MACH3'
_diffrn_measurement_method       ω-2θ
_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  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2723
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0593P)²+0.0855P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                1527
_reflns_number_total             2503
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6057.cif
_cod_data_source_block           I
_cod_database_code               2201959
_cod_database_fobs_code          2201959
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
Cl1 1.30518(13) 0.31259(12) 0.43443(6) 0.0939(3) Uani d . 1 . . Cl
C1 1.1650(4) 0.3165(3) 0.53956(19) 0.0599(6) Uani d . 1 . . C
C2 1.2396(4) 0.4034(3) 0.63867(19) 0.0586(6) Uani d . 1 . . C
H2 1.3653 0.4646 0.6498 0.070 Uiso calc R 1 . . H
C3 1.1281(3) 0.3998(3) 0.72144(18) 0.0520(6) Uani d . 1 . . C
H3 1.1787 0.4594 0.7888 0.062 Uiso calc R 1 . . H
C4 0.9406(3) 0.3085(3) 0.70658(18) 0.0483(5) Uani d . 1 . . C
C5 0.8667(4) 0.2255(3) 0.6043(2) 0.0653(7) Uani d . 1 . . C
H5 0.7400 0.1662 0.5920 0.078 Uiso calc R 1 . . H
C6 0.9769(4) 0.2298(4) 0.5216(2) 0.0703(8) Uani d . 1 . . C
H6 0.9254 0.1744 0.4532 0.084 Uiso calc R 1 . . H
C7 0.8276(3) 0.2997(3) 0.79634(18) 0.0503(6) Uani d . 1 . . C
H7 0.8738 0.3644 0.8627 0.060 Uiso calc R 1 . . H
N1 0.6640(3) 0.2020(2) 0.78283(15) 0.0507(5) Uani d . 1 . . N
N2 0.5517(3) 0.1937(2) 0.86630(14) 0.0474(5) Uani d . 1 . . N
C8 0.5795(3) 0.2824(3) 0.96927(17) 0.0452(5) Uani d . 1 . . C
O1 0.7185(2) 0.3842(2) 1.01258(12) 0.0548(4) Uani d . 1 . . O
N3 0.4083(3) 0.2233(2) 1.00901(14) 0.0461(4) Uani d . 1 . . N
N4 0.2821(3) 0.1039(2) 0.93391(15) 0.0511(5) Uani d . 1 . . N
C9 0.3485(3) 0.2796(3) 1.10770(18) 0.0488(5) Uani d . 1 . . C
O2 0.4589(2) 0.3780(2) 1.17304(14) 0.0636(5) Uani d . 1 . . O
C10 0.1472(4) 0.2092(3) 1.1229(2) 0.0641(7) Uani d . 1 . . C
H10A 0.1273 0.2400 1.1965 0.096 Uiso calc R 1 . . H
H10B 0.1307 0.0820 1.1097 0.096 Uiso calc R 1 . . H
H10C 0.0531 0.2599 1.0725 0.096 Uiso calc R 1 . . H
C11 0.3725(3) 0.0897(3) 0.85118(19) 0.0475(5) Uani d . 1 . . C
C12 0.2981(4) -0.0240(3) 0.7496(2) 0.0619(7) Uani d . 1 . . C
H12A 0.1620 -0.0657 0.7490 0.093 Uiso calc R 1 . . H
H12B 0.3727 -0.1240 0.7467 0.093 Uiso calc R 1 . . H
H12C 0.3115 0.0439 0.6873 0.093 Uiso calc 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 120.6(2) ?
C2 C1 Cl1 120.7(2) ?
C6 C1 Cl1 118.77(19) ?
C1 C2 C3 119.5(2) ?
C1 C2 H2 120.3 ?
C3 C2 H2 120.3 ?
C2 C3 C4 121.1(2) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
C5 C4 C3 118.2(2) ?
C5 C4 C7 121.5(2) ?
C3 C4 C7 120.38(19) ?
C6 C5 C4 120.9(2) ?
C6 C5 H5 119.6 ?
C4 C5 H5 119.6 ?
C5 C6 C1 119.8(2) ?
C5 C6 H6 120.1 ?
C1 C6 H6 120.1 ?
N1 C7 C4 118.7(2) ?
N1 C7 H7 120.6 ?
C4 C7 H7 120.6 ?
C7 N1 N2 119.93(18) ?
N1 N2 C11 120.01(17) ?
N1 N2 C8 131.24(17) ?
C11 N2 C8 108.66(19) ?
O1 C8 N2 128.4(2) ?
O1 C8 N3 129.4(2) ?
N2 C8 N3 102.13(17) ?
C8 N3 N4 112.27(18) ?
C8 N3 C9 127.54(17) ?
N4 N3 C9 120.01(18) ?
C11 N4 N3 104.64(17) ?
O2 C9 N3 119.8(2) y
O2 C9 C10 124.5(2) y
N3 C9 C10 115.73(19) y
C9 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C9 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
N4 C11 N2 112.30(18) y
N4 C11 C12 125.2(2) y
N2 C11 C12 122.5(2) y
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
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
Cl1 C1 . 1.730(3) y
C1 C2 . 1.366(3) ?
C1 C6 . 1.377(4) ?
C2 C3 . 1.367(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.387(3) ?
C4 C7 . 1.447(3) y
C5 C6 . 1.360(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.271(3) y
C7 H7 . 0.9300 ?
N1 N2 . 1.378(2) y
N2 C11 . 1.381(3) y
N2 C8 . 1.387(3) y
C8 O1 . 1.209(2) y
C8 N3 . 1.387(3) y
N3 N4 . 1.399(2) y
N3 C9 . 1.403(3) y
N4 C11 . 1.279(3) y
C9 O2 . 1.197(3) y
C9 C10 . 1.479(3) y
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.481(3) y
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
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
C7 H7 O1 . 0.93 2.28 2.938(3) 127
C2 H2 O2 2_767 0.93 2.52 3.162(3) 126
C12 H12B O2 2_657 0.96 2.52 3.414(3) 154
C10 H10C O1 1_455 0.96 2.61 3.499(3) 154
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654689
