#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/61/2226105.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_2226105
loop_
_publ_author_name
'Bunker, Kevin D.'
'Moore, Curtis'
'Palmer, Cynthia L.'
'Rheingold, Arnold L.'
'Yanovsky, Alex'
_publ_section_title
;
 2-Chloro-4-(1H-pyrazol-1-yl)-5-(trifluoromethyl)pyrimidine
;
_journal_coeditor_code           EZ2213
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1448
_journal_paper_doi               10.1107/S1600536810018854
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H4 Cl F3 N4'
_chemical_formula_moiety         'C8 H4 Cl F3 N4'
_chemical_formula_sum            'C8 H4 Cl F3 N4'
_chemical_formula_weight         248.60
_chemical_name_systematic
;
2-Chloro-4-(1H-pyrazol-1-yl)-5-(trifluoromethyl)pyrimidine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5776(3)
_cell_length_b                   7.7117(4)
_cell_length_c                   21.8335(12)
_cell_measurement_reflns_used    2204
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.50
_cell_measurement_theta_min      4.05
_cell_volume                     939.12(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.044
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3416
_diffrn_reflns_theta_full        61.9
_diffrn_reflns_theta_max         61.9
_diffrn_reflns_theta_min         4.0
_exptl_absorpt_coefficient_mu    3.896
_exptl_absorpt_correction_T_max  0.697
_exptl_absorpt_correction_T_min  0.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.22
_refine_ls_abs_structure_details 'Flack (1983), 503 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.033
_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)+(0.048P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.079
_refine_ls_wR_factor_ref         0.082
_reflns_number_gt                1273
_reflns_number_total             1402
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2213.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_database_code               2226105
_cod_database_fobs_code          2226105
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
Cl Cl1 0.18059(15) 0.39628(9) 0.50346(4) 0.0390(2) Uani d . 1 . .
F F1 0.7206(4) 1.0219(2) 0.35103(8) 0.0430(5) Uani d . 1 . .
F F2 0.4712(4) 0.9283(2) 0.28305(8) 0.0450(5) Uani d . 1 . .
F F3 0.3535(5) 1.0974(2) 0.35501(11) 0.0629(7) Uani d . 1 . .
N N1 0.8456(5) 0.7028(3) 0.30856(11) 0.0326(6) Uani d . 1 . .
N N2 0.7484(5) 0.5994(3) 0.35248(10) 0.0262(5) Uani d . 1 . .
N N3 0.1542(5) 0.7067(3) 0.45907(11) 0.0308(6) Uani d . 1 . .
N N4 0.4754(5) 0.5271(3) 0.42520(10) 0.0272(6) Uani d . 1 . .
C C1 0.8693(6) 0.4455(4) 0.35742(13) 0.0312(7) Uani d . 1 . .
H H1A 0.8338 0.3531 0.3848 0.037 Uiso calc R 1 . .
C C2 1.0494(6) 0.4503(4) 0.31581(13) 0.0312(7) Uani d . 1 . .
H H2A 1.1661 0.3635 0.3079 0.037 Uiso calc R 1 . .
C C3 1.0253(6) 0.6127(4) 0.28693(13) 0.0332(7) Uani d . 1 . .
H H3A 1.1282 0.6524 0.2552 0.040 Uiso calc R 1 . .
C C4 0.5510(6) 0.6502(3) 0.38708(12) 0.0250(6) Uani d . 1 . .
C C5 0.4336(6) 0.8113(4) 0.38345(13) 0.0283(6) Uani d . 1 . .
C C6 0.2380(6) 0.8301(3) 0.42115(13) 0.0304(7) Uani d . 1 . .
H H6A 0.1561 0.9381 0.4204 0.037 Uiso calc R 1 . .
C C7 0.2831(6) 0.5640(3) 0.45766(12) 0.0296(7) Uani d . 1 . .
C C8 0.4981(7) 0.9624(4) 0.34258(14) 0.0378(8) Uani d . 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
Cl1 0.0460(5) 0.0364(3) 0.0347(4) -0.0015(3) 0.0081(4) 0.0070(3)
F1 0.0604(15) 0.0304(8) 0.0382(10) -0.0103(9) 0.0101(10) -0.0007(7)
F2 0.0489(13) 0.0564(12) 0.0298(10) 0.0079(10) -0.0012(8) 0.0164(8)
F3 0.0824(18) 0.0377(10) 0.0685(14) 0.0283(12) 0.0320(13) 0.0215(10)
N1 0.0390(16) 0.0315(12) 0.0272(14) 0.0008(12) 0.0052(12) 0.0051(10)
N2 0.0341(15) 0.0238(10) 0.0208(11) 0.0022(11) -0.0010(10) 0.0006(9)
N3 0.0295(15) 0.0341(13) 0.0288(14) 0.0000(12) 0.0027(11) -0.0013(10)
N4 0.0355(16) 0.0256(10) 0.0205(12) -0.0014(11) -0.0022(11) -0.0010(9)
C1 0.043(2) 0.0259(14) 0.0242(14) 0.0034(13) -0.0011(14) -0.0004(11)
C2 0.0343(19) 0.0304(14) 0.0288(16) 0.0047(12) -0.0038(14) -0.0053(12)
C3 0.038(2) 0.0353(15) 0.0262(15) 0.0021(15) 0.0067(13) -0.0006(13)
C4 0.0296(16) 0.0269(13) 0.0185(13) -0.0009(11) -0.0032(13) -0.0021(11)
C5 0.0361(18) 0.0272(14) 0.0215(14) 0.0029(12) -0.0055(14) -0.0006(12)
C6 0.0332(18) 0.0269(13) 0.0312(15) 0.0043(12) -0.0014(14) -0.0001(11)
C7 0.038(2) 0.0311(15) 0.0198(13) -0.0031(13) -0.0031(13) 0.0008(11)
C8 0.050(2) 0.0337(15) 0.0300(17) 0.0120(15) 0.0064(15) 0.0052(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C3 N1 N2 . . 104.4(2) ?
N1 N2 C1 . . 111.6(3) ?
N1 N2 C4 . . 122.2(2) ?
C1 N2 C4 . . 126.2(2) ?
C7 N3 C6 . . 112.8(3) ?
C7 N4 C4 . . 116.1(3) ?
C2 C1 N2 . . 106.8(3) ?
C2 C1 H1A . . 126.6 ?
N2 C1 H1A . . 126.6 ?
C1 C2 C3 . . 104.7(3) ?
C1 C2 H2A . . 127.6 ?
C3 C2 H2A . . 127.6 ?
N1 C3 C2 . . 112.6(3) ?
N1 C3 H3A . . 123.7 ?
C2 C3 H3A . . 123.7 ?
N4 C4 N2 . . 112.9(2) ?
N4 C4 C5 . . 121.2(3) ?
N2 C4 C5 . . 125.9(3) ?
C6 C5 C4 . . 115.4(3) ?
C6 C5 C8 . . 117.5(3) ?
C4 C5 C8 . . 127.1(3) ?
N3 C6 C5 . . 124.7(3) ?
N3 C6 H6A . . 117.6 ?
C5 C6 H6A . . 117.6 ?
N3 C7 N4 . . 129.7(3) ?
N3 C7 Cl1 . . 115.5(2) ?
N4 C7 Cl1 . . 114.7(2) ?
F2 C8 F1 . . 107.9(3) ?
F2 C8 F3 . . 106.4(3) ?
F1 C8 F3 . . 105.3(3) ?
F2 C8 C5 . . 113.4(3) ?
F1 C8 C5 . . 113.9(3) ?
F3 C8 C5 . . 109.6(3) ?
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 C7 . 1.732(3) ?
F1 C8 . 1.336(4) ?
F2 C8 . 1.334(4) ?
F3 C8 . 1.345(4) ?
N1 C3 . 1.308(4) ?
N1 N2 . 1.360(3) ?
N2 C1 . 1.369(4) ?
N2 C4 . 1.392(4) ?
N3 C7 . 1.315(4) ?
N3 C6 . 1.345(4) ?
N4 C7 . 1.316(4) ?
N4 C4 . 1.331(4) ?
C1 C2 . 1.355(5) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.408(4) ?
C2 H2A . 0.9500 ?
C3 H3A . 0.9500 ?
C4 C5 . 1.406(4) ?
C5 C6 . 1.374(5) ?
C5 C8 . 1.511(4) ?
C6 H6A . 0.9500 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745142
