#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228333.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228333
loop_
_publ_author_name
'Feng, Zhi-Qiang'
'Yang, Xiao-Li'
'Ye, Yuan-Feng'
'Dong, Tao'
_publ_section_title
;
 2-Benzylsulfanyl-3-(2,2,2-trifluoroethoxy)pyridine
;
_journal_coeditor_code           HB5702
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3093
_journal_paper_doi               10.1107/S1600536810043308
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H12 F3 N O S'
_chemical_formula_moiety         'C14 H12 F3 N O S'
_chemical_formula_sum            'C14 H12 F3 N O S'
_chemical_formula_weight         299.31
_chemical_melting_point          353
_chemical_name_systematic
;
2-Benzylsulfanyl-3-(2,2,2-trifluoroethoxy)pyridine
;
_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                 97.32(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3770(17)
_cell_length_b                   16.860(3)
_cell_length_c                   10.144(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1421.0(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2758
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.282
_refine_ls_extinction_coef       0.049(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0580
_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)+(0.027P)²+2.174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                1716
_reflns_number_total             2575
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5702.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228333
_cod_database_fobs_code          2228333
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.18955(13) 0.37494(6) 0.26098(10) 0.0562(3) Uani d . 1 . .
O O1 -0.0642(3) 0.33867(16) 0.0614(3) 0.0602(8) Uani d . 1 . .
N N1 0.2971(4) 0.45168(18) 0.0576(3) 0.0516(8) Uani d . 1 . .
F F1 -0.2695(4) 0.21214(19) 0.1032(4) 0.1275(14) Uani d . 1 . .
F F2 -0.4629(4) 0.2729(2) -0.0088(4) 0.1367(14) Uani d . 1 . .
F F3 -0.3439(4) 0.3240(2) 0.1674(3) 0.1163(11) Uani d . 1 . .
C C1 -0.3180(6) 0.2823(3) 0.0625(6) 0.0831(15) Uani d . 1 . .
C C2 -0.2097(5) 0.3222(3) -0.0197(4) 0.0667(12) Uani d . 1 . .
H H2A -0.1897 0.2882 -0.0930 0.080 Uiso calc R 1 . .
H H2B -0.2582 0.3710 -0.0560 0.080 Uiso calc R 1 . .
C C3 0.0459(4) 0.3844(2) 0.0070(4) 0.0463(9) Uani d . 1 . .
C C4 0.0345(5) 0.4081(3) -0.1235(4) 0.0607(11) Uani d . 1 . .
H H4A -0.0530 0.3936 -0.1846 0.073 Uiso calc R 1 . .
C C5 0.1580(5) 0.4542(3) -0.1607(4) 0.0678(12) Uani d . 1 . .
H H5A 0.1544 0.4714 -0.2482 0.081 Uiso calc R 1 . .
C C6 0.2844(5) 0.4742(2) -0.0694(4) 0.0592(11) Uani d . 1 . .
H H6A 0.3661 0.5051 -0.0966 0.071 Uiso calc R 1 . .
C C7 0.1804(4) 0.4077(2) 0.0952(3) 0.0427(8) Uani d . 1 . .
C C8 0.3643(5) 0.4284(2) 0.3398(4) 0.0550(10) Uani d . 1 . .
H H8A 0.4075 0.4004 0.4201 0.066 Uiso calc R 1 . .
H H8B 0.4463 0.4285 0.2804 0.066 Uiso calc R 1 . .
C C9 0.3294(4) 0.5127(2) 0.3752(3) 0.0432(9) Uani d . 1 . .
C C10 0.4057(4) 0.5758(2) 0.3243(4) 0.0499(9) Uani d . 1 . .
H H10A 0.4780 0.5663 0.2637 0.060 Uiso calc R 1 . .
C C11 0.3776(5) 0.6527(2) 0.3611(4) 0.0591(11) Uani d . 1 . .
H H11A 0.4310 0.6943 0.3254 0.071 Uiso calc R 1 . .
C C12 0.2721(5) 0.6681(3) 0.4494(5) 0.0704(13) Uani d . 1 . .
H H12A 0.2528 0.7200 0.4739 0.084 Uiso calc R 1 . .
C C13 0.1939(5) 0.6058(3) 0.5023(5) 0.0730(13) Uani d . 1 . .
H H13A 0.1226 0.6157 0.5635 0.088 Uiso calc R 1 . .
C C14 0.2214(5) 0.5291(3) 0.4647(4) 0.0593(11) Uani d . 1 . .
H H14A 0.1668 0.4877 0.4997 0.071 Uiso calc R 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'
S S 0.1246 0.1234 '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
C7 S1 C8 . . 101.50(18) ?
C3 O1 C2 . . 116.9(3) ?
C7 N1 C6 . . 117.9(3) ?
F1 C1 F3 . . 107.8(5) ?
F1 C1 F2 . . 106.8(4) ?
F3 C1 F2 . . 105.6(4) ?
F1 C1 C2 . . 113.9(4) ?
F3 C1 C2 . . 113.0(4) ?
F2 C1 C2 . . 109.2(5) ?
O1 C2 C1 . . 108.0(4) ?
O1 C2 H2A . . 110.1 ?
C1 C2 H2A . . 110.1 ?
O1 C2 H2B . . 110.1 ?
C1 C2 H2B . . 110.1 ?
H2A C2 H2B . . 108.4 ?
O1 C3 C4 . . 125.7(3) ?
O1 C3 C7 . . 115.3(3) ?
C4 C3 C7 . . 119.0(3) ?
C3 C4 C5 . . 117.6(4) ?
C3 C4 H4A . . 121.2 ?
C5 C4 H4A . . 121.2 ?
C6 C5 C4 . . 119.9(4) ?
C6 C5 H5A . . 120.1 ?
C4 C5 H5A . . 120.1 ?
N1 C6 C5 . . 123.2(4) ?
N1 C6 H6A . . 118.4 ?
C5 C6 H6A . . 118.4 ?
N1 C7 C3 . . 122.4(3) ?
N1 C7 S1 . . 120.5(3) ?
C3 C7 S1 . . 117.0(3) ?
C9 C8 S1 . . 113.8(3) ?
C9 C8 H8A . . 108.8 ?
S1 C8 H8A . . 108.8 ?
C9 C8 H8B . . 108.8 ?
S1 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C10 C9 C14 . . 117.7(4) ?
C10 C9 C8 . . 121.8(3) ?
C14 C9 C8 . . 120.5(4) ?
C9 C10 C11 . . 121.5(4) ?
C9 C10 H10A . . 119.2 ?
C11 C10 H10A . . 119.2 ?
C12 C11 C10 . . 120.3(4) ?
C12 C11 H11A . . 119.8 ?
C10 C11 H11A . . 119.8 ?
C11 C12 C13 . . 119.4(4) ?
C11 C12 H12A . . 120.3 ?
C13 C12 H12A . . 120.3 ?
C14 C13 C12 . . 120.2(4) ?
C14 C13 H13A . . 119.9 ?
C12 C13 H13A . . 119.9 ?
C13 C14 C9 . . 121.0(4) ?
C13 C14 H14A . . 119.5 ?
C9 C14 H14A . . 119.5 ?
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
S1 C7 . 1.762(4) ?
S1 C8 . 1.816(4) ?
O1 C3 . 1.371(4) ?
O1 C2 . 1.409(4) ?
N1 C7 . 1.321(4) ?
N1 C6 . 1.334(5) ?
F1 C1 . 1.300(6) ?
F2 C1 . 1.341(6) ?
F3 C1 . 1.316(6) ?
C1 C2 . 1.472(6) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.374(5) ?
C3 C7 . 1.403(5) ?
C4 C5 . 1.385(6) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.358(5) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C8 C9 . 1.504(5) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.375(5) ?
C9 C14 . 1.389(5) ?
C10 C11 . 1.378(5) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.361(6) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.382(6) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.375(6) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
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
C3 O1 C2 C1 . . . . -172.3(4) ?
F1 C1 C2 O1 . . . . -66.8(6) ?
F3 C1 C2 O1 . . . . 56.8(6) ?
F2 C1 C2 O1 . . . . 174.0(4) ?
C2 O1 C3 C4 . . . . -7.7(6) ?
C2 O1 C3 C7 . . . . 172.6(3) ?
O1 C3 C4 C5 . . . . -179.8(4) ?
C7 C3 C4 C5 . . . . -0.1(6) ?
C3 C4 C5 C6 . . . . 0.1(6) ?
C7 N1 C6 C5 . . . . 0.1(6) ?
C4 C5 C6 N1 . . . . -0.1(7) ?
C6 N1 C7 C3 . . . . -0.1(5) ?
C6 N1 C7 S1 . . . . 179.5(3) ?
O1 C3 C7 N1 . . . . 179.8(3) ?
C4 C3 C7 N1 . . . . 0.1(6) ?
O1 C3 C7 S1 . . . . 0.3(4) ?
C4 C3 C7 S1 . . . . -179.5(3) ?
C8 S1 C7 N1 . . . . 7.5(3) ?
C8 S1 C7 C3 . . . . -173.0(3) ?
C7 S1 C8 C9 . . . . 81.3(3) ?
S1 C8 C9 C10 . . . . -120.4(3) ?
S1 C8 C9 C14 . . . . 61.7(4) ?
C14 C9 C10 C11 . . . . 0.5(5) ?
C8 C9 C10 C11 . . . . -177.5(3) ?
C9 C10 C11 C12 . . . . -0.1(6) ?
C10 C11 C12 C13 . . . . 0.3(6) ?
C11 C12 C13 C14 . . . . -0.8(7) ?
C12 C13 C14 C9 . . . . 1.1(7) ?
C10 C9 C14 C13 . . . . -0.9(6) ?
C8 C9 C14 C13 . . . . 177.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231198
