#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/25/2202550.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_2202550
loop_
_publ_author_name
'Thamotharan, S.'
'Parthasarathi, V.'
'Kavali, Jyoti R.'
'Badami, Bharati'
'Schenk, Kurt J.'
_publ_section_title
4-Amino-2-(p-chlorophenyl)-5-methyl-3,4-dihydro-2H-1,2,4-triazol-3-one
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o964
_journal_page_last               o966
_journal_paper_doi               10.1107/S1600536803012480
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C9 H9 Cl N4 O'
_chemical_formula_moiety         'C9 H9 Cl N4 O'
_chemical_formula_sum            'C9 H9 Cl N4 O'
_chemical_formula_weight         224.65
_chemical_melting_point          458
_chemical_name_systematic
;
4-Amino-2-(p-chlorophenyl)-5-methyl-3,4-dihydro-2H-1,2,4-triazol-3-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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.09(3)
_cell_angle_beta                 90.79(3)
_cell_angle_gamma                91.89(3)
_cell_formula_units_Z            2
_cell_length_a                   4.0135(8)
_cell_length_b                   11.691(2)
_cell_length_c                   11.986(2)
_cell_measurement_reflns_used    4074
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      12.2
_cell_volume                     500.2(2)
_computing_cell_refinement       'IPDS Software Package'
_computing_data_collection       'IPDS Software Package (Stoe & Cie, 1997)'
_computing_data_reduction        'IPDS Software Package'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF99 (Beurskens et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.869
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'Plane graphite'
_diffrn_radiation_source         'sealed LFF X-ray tube, 12 x 0.4 mm'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4391
_diffrn_reflns_theta_full        27.82
_diffrn_reflns_theta_max         27.82
_diffrn_reflns_theta_min         3.92
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0422
_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)+(0.0674P)²+0.0798P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                1807
_reflns_number_total             2060
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6198.cif
_cod_data_source_block           I
_cod_original_cell_volume        500.17(16)
_cod_database_code               2202550
_cod_database_fobs_code          2202550
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 1.01725(13) 0.25508(4) 0.25344(5) 0.0687(2) Uani d . 1 . . Cl
O3 0.2956(3) 0.84827(10) 0.44989(9) 0.0522(3) Uani d . 1 . . O
N1 0.5942(4) 0.74844(12) 0.14814(11) 0.0459(3) Uani d . 1 . . N
N2 0.5474(3) 0.73160(11) 0.25536(10) 0.0411(3) Uani d . 1 . . N
N4 0.3286(3) 0.90980(11) 0.28987(10) 0.0414(3) Uani d . 1 . . N
N41 0.1680(5) 1.02716(13) 0.34326(14) 0.0534(4) Uani d . 1 . . N
H411 0.311(6) 1.084(2) 0.406(2) 0.072(6) Uiso d . 1 . . H
H412 0.000(8) 1.018(3) 0.380(3) 0.086(8) Uiso d . 1 . . H
C3 0.3821(4) 0.83051(12) 0.34512(12) 0.0396(3) Uani d . 1 . . C
C5 0.4575(4) 0.85647(13) 0.17266(13) 0.0427(3) Uani d . 1 . . C
C6 0.6598(4) 0.61839(12) 0.25724(12) 0.0393(3) Uani d . 1 . . C
C7 0.7941(5) 0.52468(15) 0.14989(14) 0.0513(4) Uani d . 1 . . C
H7 0.8086 0.5368 0.0786 0.062 Uiso calc R 1 . . H
C8 0.9069(5) 0.41330(16) 0.14796(16) 0.0554(4) Uani d . 1 . . C
H8 0.9994 0.3510 0.0761 0.066 Uiso calc R 1 . . H
C9 0.8809(4) 0.39557(14) 0.25356(16) 0.0488(4) Uani d . 1 . . C
C10 0.7467(5) 0.48814(16) 0.36130(15) 0.0538(4) Uani d . 1 . . C
H10 0.7311 0.4750 0.4320 0.065 Uiso calc R 1 . . H
C11 0.6354(5) 0.60032(15) 0.36411(14) 0.0506(4) Uani d . 1 . . C
H11 0.5454 0.6628 0.4364 0.061 Uiso calc R 1 . . H
C51 0.4467(5) 0.91773(17) 0.08833(16) 0.0577(4) Uani d . 1 . . C
H511 0.5387 0.8618 0.0094 0.086 Uiso calc R 1 . . H
H512 0.5747 0.9978 0.1259 0.086 Uiso calc R 1 . . H
H513 0.2196 0.9333 0.0751 0.086 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'
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'
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
C5 N1 N2 104.81(12) yes
C3 N2 N1 111.97(11) yes
C3 N2 C6 128.90(12) ?
N1 N2 C6 119.10(11) ?
C5 N4 C3 109.34(12) yes
C5 N4 N41 124.21(13) ?
C3 N4 N41 126.46(12) ?
N4 N41 H411 105.8(16) yes
N4 N41 H412 108(2) yes
H411 N41 H412 106(2) yes
O3 C3 N2 130.39(13) ?
O3 C3 N4 126.73(13) ?
N2 C3 N4 102.89(11) yes
N1 C5 N4 110.99(13) yes
N1 C5 C51 125.64(13) ?
N4 C5 C51 123.36(14) ?
C7 C6 C11 119.98(13) ?
C7 C6 N2 118.75(13) ?
C11 C6 N2 121.28(13) ?
C8 C7 C6 120.53(15) ?
C8 C7 H7 119.7 ?
C6 C7 H7 119.7 ?
C9 C8 C7 119.31(15) ?
C9 C8 H8 120.3 ?
C7 C8 H8 120.3 ?
C8 C9 C10 120.81(14) ?
C8 C9 Cl1 120.36(13) ?
C10 C9 Cl1 118.84(13) ?
C9 C10 C11 120.16(15) ?
C9 C10 H10 119.9 ?
C11 C10 H10 119.9 ?
C10 C11 C6 119.22(14) ?
C10 C11 H11 120.4 ?
C6 C11 H11 120.4 ?
C5 C51 H511 109.5 ?
C5 C51 H512 109.5 ?
H511 C51 H512 109.5 ?
C5 C51 H513 109.5 ?
H511 C51 H513 109.5 ?
H512 C51 H513 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 C9 . 1.7477(16) ?
O3 C3 . 1.2329(17) ?
N1 C5 . 1.3017(19) yes
N1 N2 . 1.4001(16) yes
N2 C3 . 1.3682(18) yes
N2 C6 . 1.4220(18) ?
N4 C5 . 1.3687(18) yes
N4 C3 . 1.3828(18) yes
N4 N41 . 1.4063(17) ?
N41 H411 . 0.92(2) ?
N41 H412 . 0.84(3) ?
C5 C51 . 1.482(2) ?
C6 C7 . 1.386(2) ?
C6 C11 . 1.394(2) ?
C7 C8 . 1.383(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.377(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.383(2) ?
C10 C11 . 1.386(2) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C51 H511 . 0.9600 ?
C51 H512 . 0.9600 ?
C51 H513 . 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
_geom_hbond_publ_flag
N41 H411 O3 2_676 0.92(2) 2.17(2) 3.043(3) 159(2) yes
N41 H412 O3 2_576 0.84(3) 2.30(3) 2.958(2) 135(2) yes
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
C5 N1 N2 C3 -0.16(17)
C5 N1 N2 C6 177.82(13)
N1 N2 C3 O3 179.45(15)
C6 N2 C3 O3 1.7(3)
N1 N2 C3 N4 -0.19(15)
C6 N2 C3 N4 -177.92(13)
C5 N4 C3 O3 -179.20(15)
N41 N4 C3 O3 0.8(3)
C5 N4 C3 N2 0.46(16)
N41 N4 C3 N2 -179.57(15)
N2 N1 C5 N4 0.46(17)
N2 N1 C5 C51 178.96(15)
C3 N4 C5 N1 -0.61(18)
N41 N4 C5 N1 179.42(14)
C3 N4 C5 C51 -179.15(14)
N41 N4 C5 C51 0.9(2)
C3 N2 C6 C7 173.75(15)
N1 N2 C6 C7 -3.8(2)
C3 N2 C6 C11 -5.9(2)
N1 N2 C6 C11 176.50(14)
C11 C6 C7 C8 -0.5(3)
N2 C6 C7 C8 179.87(15)
C6 C7 C8 C9 0.8(3)
C7 C8 C9 C10 -0.6(3)
C7 C8 C9 Cl1 179.34(14)
C8 C9 C10 C11 0.2(3)
Cl1 C9 C10 C11 -179.78(14)
C9 C10 C11 C6 0.1(3)
C7 C6 C11 C10 0.0(3)
N2 C6 C11 C10 179.67(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9271399
