#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/41/2234100.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_2234100
loop_
_publ_author_name
'Ren, Dong-mei'
'Wang, Yong-yi'
_publ_section_title
;
 1-(4-Chloro-2-fluorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazol-5(4H)-one
;
_journal_coeditor_code           BQ2341
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1048
_journal_paper_doi               10.1107/S1600536812009452
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H7 Cl F3 N3 O'
_chemical_formula_moiety         'C10 H7 Cl F3 N3 O'
_chemical_formula_sum            'C10 H7 Cl F3 N3 O'
_chemical_formula_weight         277.64
_chemical_name_systematic
;
1-(4-Chloro-2-fluorophenyl)-4-difluoromethyl-3-methyl-1H-
1,2,4-triazol-5(4H)-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.91(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.286(3)
_cell_length_b                   13.610(3)
_cell_length_c                   11.231(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     2294.3(8)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_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'
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4290
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_correction_T_min  0.8987
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.339
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0503
_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)+(0.0730P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                1273
_reflns_number_total             2115
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2341.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234100
_cod_database_fobs_code          2234100
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_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_symmetry_multiplicity
Cl Cl 0.07385(7) 0.56530(8) 0.15418(11) 0.1001(5) Uani d . 1 1
O O 0.44175(13) 0.54039(17) -0.12275(18) 0.0621(6) Uani d . 1 1
F F1 0.26705(12) 0.64405(16) -0.14770(16) 0.0796(6) Uani d . 1 1
N N1 0.42189(15) 0.65403(18) 0.0253(2) 0.0529(6) Uani d . 1 1
C C1 0.3335(2) 0.6085(2) 0.1748(3) 0.0637(9) Uani d . 1 1
H H1A 0.3846 0.6094 0.2348 0.076 Uiso calc R 1 1
N N2 0.54325(16) 0.66315(18) -0.0433(2) 0.0541(6) Uani d . 1 1
F F2 0.62510(18) 0.72262(17) -0.1740(2) 0.1082(8) Uani d . 1 1
C C2 0.2523(3) 0.5883(3) 0.2052(3) 0.0716(10) Uani d . 1 1
H H2A 0.2483 0.5761 0.2855 0.086 Uiso calc R 1 1
F F3 0.68716(13) 0.62152(16) -0.0370(2) 0.0902(7) Uani d . 1 1
N N3 0.47231(18) 0.72846(19) 0.0904(2) 0.0598(7) Uani d . 1 1
C C3 0.1768(2) 0.5862(2) 0.1157(3) 0.0650(9) Uani d . 1 1
C C4 0.1812(2) 0.6026(2) -0.0036(3) 0.0643(9) Uani d . 1 1
H H4A 0.1304 0.5994 -0.0639 0.077 Uiso calc R 1 1
C C5 0.2627(2) 0.6237(2) -0.0314(3) 0.0547(8) Uani d . 1 1
C C6 0.3396(2) 0.6273(2) 0.0557(3) 0.0519(7) Uani d . 1 1
C C7 0.4651(2) 0.6095(2) -0.0559(3) 0.0519(7) Uani d . 1 1
C C8 0.5439(2) 0.7331(2) 0.0472(3) 0.0576(8) Uani d . 1 1
C C9 0.6171(3) 0.8030(3) 0.0887(4) 0.0860(11) Uani d . 1 1
H H9A 0.6034 0.8418 0.1541 0.129 Uiso calc R 1 1
H H9B 0.6242 0.8454 0.0228 0.129 Uiso calc R 1 1
H H9C 0.6714 0.7674 0.1160 0.129 Uiso calc R 1 1
C C10 0.6099(2) 0.6433(3) -0.1112(3) 0.0653(9) Uani d . 1 1
H H10A 0.5914 0.5883 -0.1667 0.078 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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
C7 N1 N3 112.6(2)
C7 N1 C6 127.8(3)
N3 N1 C6 119.4(2)
C2 C1 C6 120.4(3)
C2 C1 H1A 119.8
C6 C1 H1A 119.8
C7 N2 C8 108.8(3)
C7 N2 C10 122.8(3)
C8 N2 C10 128.4(3)
C1 C2 C3 119.5(3)
C1 C2 H2A 120.2
C3 C2 H2A 120.2
C8 N3 N1 105.3(2)
C4 C3 C2 121.3(3)
C4 C3 Cl 119.0(3)
C2 C3 Cl 119.7(3)
C5 C4 C3 118.1(3)
C5 C4 H4A 120.9
C3 C4 H4A 120.9
F1 C5 C4 118.5(3)
F1 C5 C6 119.2(3)
C4 C5 C6 122.3(3)
C5 C6 C1 118.3(3)
C5 C6 N1 121.1(3)
C1 C6 N1 120.5(3)
O C7 N1 129.4(3)
O C7 N2 128.2(3)
N1 C7 N2 102.4(3)
N3 C8 N2 110.8(3)
N3 C8 C9 124.3(3)
N2 C8 C9 124.9(3)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
F2 C10 F3 106.6(3)
F2 C10 N2 110.3(3)
F3 C10 N2 110.3(3)
F2 C10 H10A 109.9
F3 C10 H10A 109.9
N2 C10 H10A 109.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C3 1.733(3)
O C7 1.214(3)
F1 C5 1.349(3)
N1 C7 1.365(4)
N1 N3 1.393(3)
N1 C6 1.412(4)
C1 C2 1.375(5)
C1 C6 1.383(4)
C1 H1A 0.9300
N2 C7 1.385(4)
N2 C8 1.391(4)
N2 C10 1.409(4)
F2 C10 1.334(4)
C2 C3 1.380(5)
C2 H2A 0.9300
F3 C10 1.344(4)
N3 C8 1.280(4)
C3 C4 1.373(4)
C4 C5 1.371(4)
C4 H4A 0.9300
C5 C6 1.380(4)
C8 C9 1.476(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9800
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
C10 H10A O 2_654 0.9800 2.4100 3.259(4) 144.00 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
C6 C1 C2 C3 0.5(5)
C7 N1 N3 C8 2.6(3)
C6 N1 N3 C8 177.0(2)
C1 C2 C3 C4 0.9(5)
C1 C2 C3 Cl -177.6(3)
C2 C3 C4 C5 -1.7(5)
Cl C3 C4 C5 176.9(2)
C3 C4 C5 F1 -177.1(3)
C3 C4 C5 C6 1.0(5)
F1 C5 C6 C1 178.5(3)
C4 C5 C6 C1 0.3(5)
F1 C5 C6 N1 1.4(4)
C4 C5 C6 N1 -176.8(3)
C2 C1 C6 C5 -1.1(5)
C2 C1 C6 N1 176.1(3)
C7 N1 C6 C5 -58.7(4)
N3 N1 C6 C5 127.8(3)
C7 N1 C6 C1 124.2(3)
N3 N1 C6 C1 -49.3(4)
N3 N1 C7 O 176.9(3)
C6 N1 C7 O 3.1(5)
N3 N1 C7 N2 -3.1(3)
C6 N1 C7 N2 -177.0(2)
C8 N2 C7 O -177.6(3)
C10 N2 C7 O 0.2(5)
C8 N2 C7 N1 2.5(3)
C10 N2 C7 N1 -179.8(3)
N1 N3 C8 N2 -0.8(3)
N1 N3 C8 C9 179.4(3)
C7 N2 C8 N3 -1.1(3)
C10 N2 C8 N3 -178.7(3)
C7 N2 C8 C9 178.7(3)
C10 N2 C8 C9 1.1(5)
C7 N2 C10 F2 122.1(3)
C8 N2 C10 F2 -60.6(4)
C7 N2 C10 F3 -120.5(3)
C8 N2 C10 F3 56.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8057771
