#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/02/2210235.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_2210235
loop_
_publ_author_name
'Fei-Fei Sun'
'Ning Ma'
'Zheng-Ming Li'
'Hai-Bin Song'
_publ_section_title
;
 2-Amino-4-(2,2,2-trifluoroethoxy)pyrimidine
;
_journal_coeditor_code           GH2007
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3864
_journal_page_last               o3865
_journal_paper_doi               10.1107/S1600536806029564
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C6 H6 F3 N3 O'
_chemical_formula_moiety         'C6 H6 F3 N3 O'
_chemical_formula_sum            'C6 H6 F3 N3 O'
_chemical_formula_weight         193.14
_chemical_name_systematic
;
2-amino-4-(2,2,2-trifluoroethoxy)pyrimidine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.989(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.135(6)
_cell_length_b                   10.537(5)
_cell_length_c                   13.705(7)
_cell_measurement_reflns_used    893
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.01
_cell_measurement_theta_min      3.37
_cell_volume                     1646.8(14)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_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  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8219
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.882556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.230
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0522
_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)+(0.0731P)²+0.3351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                1669
_reflns_number_total             2905
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gh2007.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210235
_cod_database_fobs_code          2210235
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O O1 0.8870(2) 0.8163(2) 0.87642(16) 0.0608(7) Uani d . 1
N N1 0.7562(2) 0.6064(3) 0.5627(2) 0.0638(8) Uani d . 1
H H1A 0.7378 0.6061 0.4962 0.077 Uiso calc R 1
H H1B 0.7519 0.5375 0.5948 0.077 Uiso calc R 1
N N2 0.8214(2) 0.7088(2) 0.72083(19) 0.0487(7) Uani d . 1
N N3 0.7972(2) 0.8199(3) 0.56197(19) 0.0519(7) Uani d . 1
C C1 0.7921(3) 0.7150(3) 0.6165(2) 0.0463(8) Uani d . 1
C C2 0.8572(3) 0.8157(3) 0.7713(2) 0.0482(8) Uani d . 1
C C3 0.8673(3) 0.9297(3) 0.7245(2) 0.0553(9) Uani d . 1
H H3 0.8934 1.0039 0.7622 0.066 Uiso calc R 1
C C4 0.8361(3) 0.9248(3) 0.6192(2) 0.0541(9) Uani d . 1
H H4 0.8421 0.9990 0.5846 0.065 Uiso calc R 1
C C5 0.8851(3) 0.6972(3) 0.9242(3) 0.0654(10) Uani d . 1
H H5A 0.9422 0.6402 0.9126 0.078 Uiso calc R 1
H H5B 0.8081 0.6588 0.8954 0.078 Uiso calc R 1
C C6 0.9141(4) 0.7209(4) 1.0369(3) 0.0708(11) Uani d . 1
F F1 0.9093(3) 0.6134(3) 1.08572(19) 0.1302(11) Uani d . 1
F F2 1.0161(3) 0.7701(3) 1.0820(2) 0.1398(12) Uani d . 1
F F3 0.8386(3) 0.7987(3) 1.0564(2) 0.1223(10) Uani d . 1
N N4 0.6358(2) 0.8388(2) 0.34097(19) 0.0522(7) Uani d . 1
H H4A 0.6103 0.9118 0.3150 0.063 Uiso calc R 1
H H4B 0.6595 0.8278 0.4071 0.063 Uiso calc R 1
N N5 0.6004(2) 0.7657(2) 0.17502(17) 0.0406(6) Uani d . 1
N N6 0.6800(2) 0.6286(2) 0.32315(18) 0.0457(6) Uani d . 1
O O2 0.56510(19) 0.68830(18) 0.01016(15) 0.0533(6) Uani d . 1
C C7 0.6388(2) 0.7415(3) 0.2780(2) 0.0406(7) Uani d . 1
C C8 0.6020(3) 0.6696(3) 0.1147(2) 0.0402(7) Uani d . 1
C C9 0.6398(3) 0.5484(3) 0.1510(2) 0.0475(8) Uani d . 1
H H9 0.6389 0.4813 0.1066 0.057 Uiso calc R 1
C C10 0.6783(3) 0.5348(3) 0.2562(2) 0.0479(8) Uani d . 1
H H10 0.7051 0.4553 0.2835 0.057 Uiso calc R 1
C C11 0.5258(3) 0.8142(3) -0.0250(2) 0.0553(9) Uani d . 1
H H11A 0.5829 0.8764 0.0137 0.066 Uiso calc R 1
H H11B 0.4517 0.8317 -0.0153 0.066 Uiso calc R 1
C C12 0.5114(3) 0.8201(3) -0.1369(2) 0.0518(8) Uani d . 1
F F4 0.47512(19) 0.93514(18) -0.17405(15) 0.0781(7) Uani d . 1
F F5 0.6078(2) 0.7955(3) -0.15665(19) 0.1011(9) Uani d . 1
F F6 0.4310(2) 0.7397(2) -0.19375(17) 0.0947(8) 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'
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
C2 O1 C5 116.4(3) yes
C1 N1 H1A 120.0 ?
C1 N1 H1B 120.0 ?
H1A N1 H1B 120.0 ?
C2 N2 C1 115.8(3) ?
C4 N3 C1 115.1(3) ?
N3 C1 N1 117.3(3) ?
N3 C1 N2 125.5(3) yes
N1 C1 N2 117.1(3) ?
N2 C2 O1 118.7(3) yes
N2 C2 C3 124.4(3) yes
O1 C2 C3 116.9(3) ?
C4 C3 C2 114.9(3) ?
C4 C3 H3 122.6 ?
C2 C3 H3 122.6 ?
N3 C4 C3 124.4(3) ?
N3 C4 H4 117.8 ?
C3 C4 H4 117.8 ?
O1 C5 C6 107.2(3) yes
O1 C5 H5A 110.3 ?
C6 C5 H5A 110.3 ?
O1 C5 H5B 110.3 ?
C6 C5 H5B 110.3 ?
H5A C5 H5B 108.5 ?
F2 C6 F3 105.8(4) yes
F2 C6 F1 107.6(4) ?
F3 C6 F1 105.9(3) ?
F2 C6 C5 114.5(3) ?
F3 C6 C5 112.4(3) ?
F1 C6 C5 110.2(3) ?
C7 N4 H4A 120.0 ?
C7 N4 H4B 120.0 ?
H4A N4 H4B 120.0 ?
C8 N5 C7 116.1(2) ?
C10 N6 C7 114.6(3) ?
C8 O2 C11 116.0(2) ?
N4 C7 N5 116.8(3) ?
N4 C7 N6 117.5(3) ?
N5 C7 N6 125.8(3) ?
N5 C8 O2 118.8(2) ?
N5 C8 C9 123.9(3) ?
O2 C8 C9 117.3(2) ?
C10 C9 C8 115.2(3) ?
C10 C9 H9 122.4 ?
C8 C9 H9 122.4 ?
N6 C10 C9 124.4(3) ?
N6 C10 H10 117.8 ?
C9 C10 H10 117.8 ?
O2 C11 C12 107.1(2) ?
O2 C11 H11A 110.3 ?
C12 C11 H11A 110.3 ?
O2 C11 H11B 110.3 ?
C12 C11 H11B 110.3 ?
H11A C11 H11B 108.5 ?
F5 C12 F6 106.3(3) ?
F5 C12 F4 107.6(3) ?
F6 C12 F4 106.0(3) ?
F5 C12 C11 114.0(3) ?
F6 C12 C11 112.5(3) ?
F4 C12 C11 109.9(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.361(4) yes
O1 C5 1.419(4) yes
N1 C1 1.350(4) yes
N1 H1A 0.8600 ?
N1 H1B 0.8600 ?
N2 C2 1.316(4) yes
N2 C1 1.352(4) yes
N3 C4 1.344(4) yes
N3 C1 1.348(4) yes
C2 C3 1.387(4) yes
C3 C4 1.362(4) yes
C3 H3 0.9300 ?
C4 H4 0.9300 ?
C5 C6 1.483(5) yes
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 F2 1.288(4) yes
C6 F3 1.323(5) yes
C6 F1 1.327(4) yes
N4 C7 1.348(4) ?
N4 H4A 0.8600 ?
N4 H4B 0.8600 ?
N5 C8 1.311(3) ?
N5 C7 1.350(4) ?
N6 C10 1.344(4) ?
N6 C7 1.355(4) yes
O2 C8 1.361(3) ?
O2 C11 1.436(3) yes
C8 C9 1.390(4) ?
C9 C10 1.363(4) ?
C9 H9 0.9300 ?
C10 H10 0.9300 ?
C11 C12 1.483(4) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 F5 1.314(4) ?
C12 F6 1.327(4) ?
C12 F4 1.330(3) ?
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
N1 H1A N6 . 0.86 2.24 3.100(7) 173
N4 H4B N3 . 0.86 2.21 2.999(6) 153
N4 H4A F4 3_675 0.86 2.46 3.258(7) 155
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
_geom_torsion_publ_flag
C4 N3 C1 N1 -178.5(3) yes
C4 N3 C1 N2 0.6(5) ?
C2 N2 C1 N3 0.3(5) ?
C2 N2 C1 N1 179.3(3) ?
C1 N2 C2 O1 179.4(3) yes
C1 N2 C2 C3 -0.8(5) ?
C5 O1 C2 N2 4.6(4) ?
C5 O1 C2 C3 -175.2(3) ?
N2 C2 C3 C4 0.4(5) ?
O1 C2 C3 C4 -179.7(3) ?
C1 N3 C4 C3 -1.0(5) ?
C2 C3 C4 N3 0.5(5) ?
C2 O1 C5 C6 -177.2(3) yes
O1 C5 C6 F2 -61.0(5) ?
O1 C5 C6 F3 59.7(4) ?
O1 C5 C6 F1 177.6(3) ?
C8 N5 C7 N4 -178.9(3) ?
C8 N5 C7 N6 1.2(4) ?
C10 N6 C7 N4 178.6(3) ?
C10 N6 C7 N5 -1.5(4) ?
C7 N5 C8 O2 -179.5(2) ?
C7 N5 C8 C9 0.2(4) ?
C11 O2 C8 N5 -0.7(4) ?
C11 O2 C8 C9 179.6(3) ?
N5 C8 C9 C10 -1.1(5) ?
O2 C8 C9 C10 178.6(3) ?
C7 N6 C10 C9 0.4(4) ?
C8 C9 C10 N6 0.7(5) ?
C8 O2 C11 C12 169.5(3) yes
O2 C11 C12 F5 -59.0(4) ?
O2 C11 C12 F6 62.2(4) ?
O2 C11 C12 F4 -179.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24736008
