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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/37/2223793.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_2223793
loop_
_publ_author_name
'Li, Yong-Hong'
'Zhang, Tao'
'Mei, Xiang-Dong'
'Ning, Jun'
_publ_section_title
;
 4,6-Bis[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]pyrimidine
;
_journal_coeditor_code           HB5156
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2865
_journal_paper_doi               10.1107/S1600536809043657
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 F6 N6'
_chemical_formula_moiety         'C14 H10 F6 N6'
_chemical_formula_sum            'C14 H10 F6 N6'
_chemical_formula_weight         376.28
_chemical_name_systematic
;
4,6-Bis[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]pyrimidine
;
_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                 99.295(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5387(14)
_cell_length_b                   16.110(6)
_cell_length_c                   11.022(5)
_cell_measurement_reflns_used    648
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1496.3(9)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8915
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0468
_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)+(0.0291P)²+1.4916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                1678
_reflns_number_total             1706
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5156.cif
_cod_data_source_block           I
_cod_original_cell_volume        1496.2(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223793
_cod_database_fobs_code          2223793
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_disorder_assembly
_atom_site_disorder_group
F F1 0.53252(12) 0.61885(7) 0.61601(11) 0.0484(3) Uani d . 1 . .
F F2 0.39212(17) 0.66320(8) 0.45033(11) 0.0610(4) Uani d . 1 . .
F F3 0.31154(14) 0.67824(7) 0.62363(12) 0.0544(3) Uani d . 1 . .
N N1 0.22004(15) 0.52452(8) 0.43231(12) 0.0284(3) Uani d . 1 . .
N N2 0.16127(15) 0.44751(8) 0.45125(11) 0.0269(3) Uani d . 1 . .
N N3 0.07685(16) 0.32384(8) 0.35077(13) 0.0311(3) Uani d . 1 . .
C C1 0.30268(18) 0.54413(10) 0.54059(14) 0.0288(3) Uani d . 1 . .
C C2 0.29725(19) 0.48203(10) 0.62924(14) 0.0310(4) Uani d . 1 . .
H H2A 0.3470 0.4829 0.7128 0.037 Uiso calc R 1 . .
C C3 0.20539(18) 0.42006(10) 0.57018(14) 0.0289(3) Uani d . 1 . .
C C4 0.1508(2) 0.34123(11) 0.62036(16) 0.0369(4) Uani d . 1 . .
H H4A 0.1750 0.3423 0.7103 0.055 Uiso calc R 1 . .
H H4B 0.2054 0.2942 0.5892 0.055 Uiso calc R 1 . .
H H4C 0.0360 0.3353 0.5945 0.055 Uiso calc R 1 . .
C C5 0.07580(17) 0.40647(10) 0.34787(13) 0.0266(3) Uani d . 1 . .
C C6 0.0000 0.45258(14) 0.2500 0.0265(4) Uani d S 1 . .
H H6A 0.0000 0.5115 0.2500 0.032 Uiso calc SR 1 . .
C C7 0.0000 0.28736(15) 0.2500 0.0331(5) Uani d S 1 . .
H H7A 0.0000 0.2284 0.2500 0.040 Uiso calc SR 1 . .
C C8 0.3840(2) 0.62608(11) 0.55639(15) 0.0342(4) Uani d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 N2 . . 103.56(13) ?
N1 N2 C3 . . 112.71(12) ?
N1 N2 C5 . . 117.12(12) ?
C3 N2 C5 . . 130.02(14) ?
C5 N3 C7 . . 114.87(15) ?
N1 C1 C2 . . 112.63(15) ?
N1 C1 C8 . . 119.21(14) ?
C2 C1 C8 . . 128.13(15) ?
C3 C2 C1 . . 105.64(14) ?
C3 C2 H2A . . 127.2 ?
C1 C2 H2A . . 127.2 ?
C2 C3 N2 . . 105.44(14) ?
C2 C3 C4 . . 129.45(15) ?
N2 C3 C4 . . 124.98(15) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N3 C5 C6 . . 123.83(15) ?
N3 C5 N2 . . 116.59(13) ?
C6 C5 N2 . . 119.57(15) ?
C5 C6 C5 2 . 114.9(2) ?
C5 C6 H6A 2 . 122.5 ?
C5 C6 H6A . . 122.5 ?
N3 C7 N3 . 2 127.6(2) ?
N3 C7 H7A . . 116.2 ?
N3 C7 H7A 2 . 116.2 ?
F2 C8 F1 . . 107.01(15) ?
F2 C8 F3 . . 107.49(16) ?
F1 C8 F3 . . 105.65(14) ?
F2 C8 C1 . . 112.77(14) ?
F1 C8 C1 . . 111.59(14) ?
F3 C8 C1 . . 111.93(14) ?
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
F1 C8 . 1.3359(19) ?
F2 C8 . 1.325(2) ?
F3 C8 . 1.336(2) ?
N1 C1 . 1.323(2) ?
N1 N2 . 1.3668(19) ?
N2 C3 . 1.377(2) ?
N2 C5 . 1.414(2) ?
N3 C5 . 1.331(2) ?
N3 C7 . 1.3319(17) ?
C1 C2 . 1.404(2) ?
C1 C8 . 1.489(2) ?
C2 C3 . 1.368(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.490(2) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 C6 . 1.3815(19) ?
C6 C5 2 1.3815(19) ?
C6 H6A . 0.9500 ?
C7 N3 2 1.3319(17) ?
C7 H7A . 0.9500 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C3 . . . . 0.68(16) ?
C1 N1 N2 C5 . . . . -175.36(13) ?
N2 N1 C1 C2 . . . . -0.63(17) ?
N2 N1 C1 C8 . . . . -179.10(13) ?
N1 C1 C2 C3 . . . . 0.37(18) ?
C8 C1 C2 C3 . . . . 178.67(15) ?
C1 C2 C3 N2 . . . . 0.07(17) ?
C1 C2 C3 C4 . . . . -175.86(16) ?
N1 N2 C3 C2 . . . . -0.47(17) ?
C5 N2 C3 C2 . . . . 174.92(14) ?
N1 N2 C3 C4 . . . . 175.69(14) ?
C5 N2 C3 C4 . . . . -8.9(3) ?
C7 N3 C5 C6 . . . . 0.9(2) ?
C7 N3 C5 N2 . . . . -177.66(11) ?
N1 N2 C5 N3 . . . . 152.46(14) ?
C3 N2 C5 N3 . . . . -22.8(2) ?
N1 N2 C5 C6 . . . . -26.16(18) ?
C3 N2 C5 C6 . . . . 158.62(13) ?
N3 C5 C6 C5 . . . 2 -0.48(11) ?
N2 C5 C6 C5 . . . 2 178.03(15) ?
C5 N3 C7 N3 . . . 2 -0.43(10) ?
N1 C1 C8 F2 . . . . -14.0(2) ?
C2 C1 C8 F2 . . . . 167.76(16) ?
N1 C1 C8 F1 . . . . -134.52(15) ?
C2 C1 C8 F1 . . . . 47.3(2) ?
N1 C1 C8 F3 . . . . 107.31(17) ?
C2 C1 C8 F3 . . . . -70.9(2) ?
