#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2010603.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_2010603
loop_
_publ_author_name
'Halcrow, Malcolm A.'
'Kilner, Colin A.'
'Thornton-Pett, Mark'
_publ_section_title
;
 2,6-Bis-(3-trifluoromethylpyrazol-1-yl)pyridine
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              213
_journal_page_last               214
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          'C13 H7 F6 N5'
_chemical_formula_moiety         'C13 H7 F6 N5'
_chemical_formula_sum            'C13 H7 F6 N5'
_chemical_formula_weight         347.24
_chemical_name_systematic
;
2,6-Bis-(3-{trifluoromethyl}pyrazol-1-yl)pyridine
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.738(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5849(11)
_cell_length_b                   11.6404(6)
_cell_length_c                   8.1150(7)
_cell_measurement_reflns_used    8690
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.26
_cell_volume                     1347.63(17)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  'local program'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full .986
_diffrn_measured_fraction_theta_max .986
_diffrn_measurement_device_type
'Nonius KappaCCD area detector diffractometer'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .056
_diffrn_reflns_av_sigmaI/netI    .043
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8690
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    .166
_exptl_absorpt_correction_T_max  .9611
_exptl_absorpt_correction_T_min  .9425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          .36
_exptl_crystal_size_mid          .27
_exptl_crystal_size_min          .24
_refine_diff_density_max         .30
_refine_diff_density_min         -.27
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          .0693
_refine_ls_R_factor_gt           .0473
_refine_ls_shift/su_max          .01
_refine_ls_shift/su_mean         .002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.7815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1391
_reflns_number_gt                1116
_reflns_number_total             1534
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1377.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_database_code               2010603
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_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_type_symbol
N1 .0000 .90938(19) -.7500 .0301(5) Uani d S 1 N
C2 .06745(12) .97009(15) -.6249(2) .0290(4) Uani d . 1 C
C3 .07162(13) 1.08899(17) -.6184(3) .0333(5) Uani d . 1 C
H3 .1197(16) 1.1240(18) -.529(3) .038(6) Uiso d . 1 H
C4 .0000 1.1483(2) -.7500 .0343(6) Uani d S 1 C
H4 .0000 1.233(3) -.7500 .035(7) Uiso d S 1 H
N5 .13781(10) .90447(14) -.4909(2) .0307(4) Uani d . 1 N
N6 .21342(11) .95933(13) -.3675(2) .0334(4) Uani d . 1 N
C7 .26270(13) .87541(15) -.2613(3) .0325(5) Uani d . 1 C
C8 .22009(13) .76699(17) -.3129(3) .0344(5) Uani d . 1 C
H8 .2437(16) .693(2) -.255(3) .049(6) Uiso d . 1 H
C9 .13995(13) .78912(16) -.4608(3) .0332(5) Uani d . 1 C
H9 .0889(15) .7429(18) -.537(3) .033(5) Uiso d . 1 H
C10 .35415(14) .90242(17) -.1116(3) .0377(5) Uani d . 1 C
F11 .35959(10) .85857(12) .04485(18) .0583(5) Uani d . 1 F
F12 .42573(9) .85687(15) -.1378(2) .0719(6) Uani d . 1 F
F13 .36999(9) 1.01383(11) -.0842(2) .0638(5) Uani d . 1 F
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
N1 .0245(10) .0333(12) .0300(12) .000 .0082(9) .000
C2 .0247(9) .0329(10) .0274(10) .0007(7) .0085(8) .0017(7)
C3 .0288(9) .0334(10) .0314(10) -.0034(8) .0056(8) -.0023(8)
C4 .0339(14) .0304(14) .0342(15) .000 .0090(12) .000
N5 .0256(8) .0312(8) .0299(9) -.0007(6) .0057(7) .0007(6)
N6 .0265(8) .0345(9) .0319(9) -.0008(6) .0041(7) .0005(6)
C7 .0283(9) .0323(10) .0323(10) .0020(7) .0076(8) .0014(8)
C8 .0321(9) .0323(10) .0346(11) .0022(8) .0093(8) .0029(8)
C9 .0298(9) .0306(10) .0350(11) -.0013(8) .0086(8) .0004(8)
C10 .0334(10) .0353(11) .0360(11) .0059(8) .0053(8) .0023(8)
F11 .0579(9) .0625(9) .0369(8) -.0007(7) .0006(6) .0085(6)
F12 .0290(7) .1090(13) .0636(11) .0092(7) .0039(7) -.0290(9)
F13 .0503(8) .0374(8) .0665(10) -.0062(6) -.0153(7) .0038(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .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
C2 N1 C2 . 2_553 116.0(2) yes
N1 C2 C3 . . 124.69(17) yes
N1 C2 N5 . . 115.35(17) yes
C3 C2 N5 . . 119.96(16) yes
H3 C3 C4 . . 123.2(14) no
H3 C3 C2 . . 119.5(14) no
C4 C3 C2 . . 117.36(18) yes
H4 C4 C3 . . 120.03(13) no
C3 C4 C3 2_553 . 119.9(3) yes
N6 N5 C9 . . 112.27(15) yes
N6 N5 C2 . . 119.05(16) yes
C9 N5 C2 . . 128.63(15) yes
C7 N6 N5 . . 103.68(15) yes
N6 C7 C8 . . 112.77(17) yes
N6 C7 C10 . . 119.31(16) yes
C8 C7 C10 . . 127.88(17) yes
H8 C8 C9 . . 128.4(13) no
H8 C8 C7 . . 127.3(13) no
C9 C8 C7 . . 104.32(17) yes
H9 C9 C8 . . 133.8(12) no
H9 C9 N5 . . 119.2(12) no
C8 C9 N5 . . 106.96(16) yes
F13 C10 F12 . . 107.86(18) no
F13 C10 F11 . . 106.15(17) no
F12 C10 F11 . . 105.23(17) no
F13 C10 C7 . . 113.42(16) no
F12 C10 C7 . . 112.07(17) no
F11 C10 C7 . . 111.60(17) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.333(2) yes
C2 C3 1.386(3) yes
C2 N5 1.417(2) yes
C3 H3 .90(2) no
C3 C4 1.380(2) yes
C4 H4 .98(3) no
N5 N6 1.360(2) yes
N5 C9 1.363(2) yes
N6 C7 1.324(2) yes
C7 C8 1.409(3) yes
C7 C10 1.487(3) yes
C8 H8 .98(2) no
C8 C9 1.364(3) yes
C9 H9 .95(2) no
C10 F13 1.322(2) no
C10 F12 1.327(2) no
C10 F11 1.339(2) no