#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/95/2209565.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_2209565
loop_
_publ_author_name
'Jing Heng'
'Hong-Jun Zhu'
'Qing-Gang Tang'
'Hong-Lan Yan'
_publ_section_title
;
 4-Difluoromethyl-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one
;
_journal_coeditor_code           JH2013
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3111
_journal_page_last               o3112
_journal_paper_doi               10.1107/S1600536806019003
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H9 F2 N3 O'
_chemical_formula_moiety         'C10 H9 F2 N3 O'
_chemical_formula_sum            'C10 H9 F2 N3 O'
_chemical_formula_weight         225.20
_chemical_name_systematic
;
4-Difluoromethyl-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-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                85.88(3)
_cell_angle_beta                 80.43(3)
_cell_angle_gamma                81.71(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2910(15)
_cell_length_b                   8.2100(16)
_cell_length_c                   8.8710(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      11
_cell_volume                     517.52(19)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo,1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  SHELXS97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_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  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2188
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.143
_refine_ls_extinction_coef       0.131(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0427
_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)+(0.06P)²+0.06P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                1422
_reflns_number_total             2019
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2013.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        517.53(19)
_cod_database_code               2209565
_cod_database_fobs_code          2209565
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
F F1 0.3603(2) 0.70240(19) 1.03226(14) 0.0951(5) Uani d . 1
F F2 0.0949(2) 0.62729(16) 1.01687(15) 0.0940(5) Uani d . 1
O O 0.1464(2) 1.06459(16) 0.81753(15) 0.0699(4) Uani d . 1
N N1 0.2319(2) 0.77975(17) 0.81876(16) 0.0526(4) Uani d . 1
N N2 0.2493(2) 0.91199(17) 0.59845(16) 0.0506(4) Uani d . 1
N N3 0.3106(2) 0.74604(19) 0.57154(18) 0.0578(4) Uani d . 1
C C1 0.3126(3) 1.0936(3) 0.2050(3) 0.0800(7) Uani d . 1
H H1A 0.3591 1.0595 0.1066 0.096 Uiso calc R 1
C C2 0.3159(3) 0.9807(3) 0.3270(2) 0.0671(6) Uani d . 1
H H2A 0.3652 0.8713 0.3110 0.081 Uiso calc R 1
C C3 0.2462(2) 1.0300(2) 0.4730(2) 0.0517(5) Uani d . 1
C C4 0.1735(3) 1.1920(2) 0.4960(2) 0.0680(6) Uani d . 1
H H4A 0.1255 1.2264 0.5941 0.082 Uiso calc R 1
C C5 0.1727(3) 1.3033(3) 0.3713(3) 0.0802(7) Uani d . 1
H H5A 0.1240 1.4130 0.3864 0.096 Uiso calc R 1
C C6 0.2422(3) 1.2550(3) 0.2261(3) 0.0756(6) Uani d . 1
H H6A 0.2415 1.3309 0.1431 0.091 Uiso calc R 1
C C7 0.3502(4) 0.4907(2) 0.7326(3) 0.0800(7) Uani d . 1
H H7A 0.3932 0.4398 0.6366 0.120 Uiso calc R 1
H H7B 0.2422 0.4442 0.7849 0.120 Uiso calc R 1
H H7C 0.4482 0.4716 0.7944 0.120 Uiso calc R 1
C C8 0.2993(3) 0.6709(2) 0.7044(2) 0.0549(5) Uani d . 1
C C9 0.2008(2) 0.9374(2) 0.7510(2) 0.0523(5) Uani d . 1
C C10 0.1977(3) 0.7519(2) 0.9793(2) 0.0632(5) Uani d . 1
H H10A 0.1331 0.8523 1.0282 0.076 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 0.0925(10) 0.1221(12) 0.0682(8) 0.0056(8) -0.0272(7) 0.0051(7)
F2 0.1118(12) 0.0779(9) 0.0878(9) -0.0315(8) 0.0053(8) 0.0140(7)
O 0.0900(11) 0.0501(8) 0.0625(9) -0.0006(7) 0.0038(7) -0.0094(6)
N1 0.0555(9) 0.0481(9) 0.0522(9) -0.0022(7) -0.0063(7) -0.0029(7)
N2 0.0526(9) 0.0469(8) 0.0507(9) -0.0013(6) -0.0073(6) -0.0049(6)
N3 0.0605(10) 0.0517(9) 0.0602(10) 0.0004(7) -0.0111(7) -0.0094(7)
C1 0.0957(18) 0.0901(18) 0.0553(13) -0.0245(14) -0.0067(11) 0.0007(11)
C2 0.0787(14) 0.0656(13) 0.0572(12) -0.0134(11) -0.0068(10) -0.0051(10)
C3 0.0432(10) 0.0562(11) 0.0571(11) -0.0099(8) -0.0110(8) 0.0011(8)
C4 0.0730(14) 0.0601(12) 0.0661(13) 0.0002(10) -0.0062(10) 0.0003(10)
C5 0.0801(16) 0.0640(14) 0.0911(18) -0.0003(11) -0.0131(13) 0.0127(12)
C6 0.0775(15) 0.0800(16) 0.0705(14) -0.0191(12) -0.0188(11) 0.0220(12)
C7 0.1015(18) 0.0522(12) 0.0810(15) 0.0067(11) -0.0136(13) -0.0046(10)
C8 0.0524(11) 0.0513(10) 0.0603(12) -0.0009(8) -0.0102(8) -0.0065(9)
C9 0.0491(10) 0.0510(10) 0.0554(11) -0.0055(8) -0.0044(8) -0.0034(8)
C10 0.0690(13) 0.0572(12) 0.0589(12) -0.0040(10) -0.0039(10) 0.0034(9)
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'
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
C8 N1 C9 108.30(15) yes
C8 N1 C10 130.39(16) yes
C9 N1 C10 121.29(15) yes
C9 N2 N3 111.71(14) yes
C9 N2 C3 128.48(15) yes
N3 N2 C3 119.80(14) yes
C8 N3 N2 105.67(14) yes
C6 C1 C2 121.0(2) ?
C6 C1 H1A 119.5 ?
C2 C1 H1A 119.5 ?
C1 C2 C3 119.9(2) ?
C1 C2 H2A 120.1 ?
C3 C2 H2A 120.1 ?
C4 C3 C2 119.81(18) ?
C4 C3 N2 120.75(17) yes
C2 C3 N2 119.43(17) yes
C3 C4 C5 119.1(2) ?
C3 C4 H4A 120.4 ?
C5 C4 H4A 120.4 ?
C6 C5 C4 121.3(2) ?
C6 C5 H5A 119.4 ?
C4 C5 H5A 119.4 ?
C1 C6 C5 118.9(2) ?
C1 C6 H6A 120.6 ?
C5 C6 H6A 120.6 ?
C8 C7 H7A 109.5 ?
C8 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C8 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N3 C8 N1 111.07(16) yes
N3 C8 C7 124.93(18) yes
N1 C8 C7 124.00(18) yes
O C9 N2 130.43(17) yes
O C9 N1 126.32(17) yes
N2 C9 N1 103.24(15) yes
F2 C10 F1 105.52(16) yes
F2 C10 N1 110.18(17) yes
F1 C10 N1 110.13(16) yes
F2 C10 H10A 110.3 ?
F1 C10 H10A 110.3 ?
N1 C10 H10A 110.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C10 1.346(2) yes
F2 C10 1.345(2) yes
O C9 1.219(2) yes
N1 C8 1.381(2) yes
N1 C9 1.392(2) yes
N1 C10 1.412(2) yes
N2 C9 1.364(2) yes
N2 N3 1.396(2) yes
N2 C3 1.423(2) yes
N3 C8 1.286(2) yes
C1 C6 1.364(3) ?
C1 C2 1.374(3) ?
C1 H1A 0.9300 ?
C2 C3 1.377(3) ?
C2 H2A 0.9300 ?
C3 C4 1.376(3) ?
C4 C5 1.383(3) ?
C4 H4A 0.9300 ?
C5 C6 1.368(3) ?
C5 H5A 0.9300 ?
C6 H6A 0.9300 ?
C7 C8 1.486(3) ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 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
C2 H2A N3 . 0.9300 2.4600 2.795(3) 102 yes
C4 H4A O . 0.9300 2.3200 2.952(2) 125 yes
C7 H7C F1 2_667 0.9600 2.4900 3.368(3) 153 yes
C10 H10A O . 0.9800 2.4600 2.857(2) 104 yes
C10 H10A O 2_577 0.9800 2.3000 3.100(2) 138 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
C9 N2 N3 C8 0.3(2)
C3 N2 N3 C8 179.51(15)
C6 C1 C2 C3 0.5(3)
C1 C2 C3 C4 0.0(3)
C1 C2 C3 N2 179.67(18)
C9 N2 C3 C4 -5.7(3)
N3 N2 C3 C4 175.19(16)
C9 N2 C3 C2 174.60(17)
N3 N2 C3 C2 -4.5(2)
C2 C3 C4 C5 -0.3(3)
N2 C3 C4 C5 -179.98(18)
C3 C4 C5 C6 0.2(3)
C2 C1 C6 C5 -0.6(4)
C4 C5 C6 C1 0.3(4)
N2 N3 C8 N1 0.4(2)
N2 N3 C8 C7 179.93(18)
C9 N1 C8 N3 -0.9(2)
C10 N1 C8 N3 -179.83(17)
C9 N1 C8 C7 179.55(19)
C10 N1 C8 C7 0.6(3)
N3 N2 C9 O 177.90(18)
C3 N2 C9 O -1.2(3)
N3 N2 C9 N1 -0.80(18)
C3 N2 C9 N1 -179.93(15)
C8 N1 C9 O -177.78(18)
C10 N1 C9 O 1.3(3)
C8 N1 C9 N2 0.99(18)
C10 N1 C9 N2 -179.96(15)
C8 N1 C10 F2 -50.0(3)
C9 N1 C10 F2 131.18(18)
C8 N1 C10 F1 66.0(3)
C9 N1 C10 F1 -112.82(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9260607
