#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/73/2017375.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_2017375
loop_
_publ_author_name
'Zhang, Zhenfeng'
'Zhang, Jinming'
'Zhang, Guisheng'
'Wang, Jange'
_publ_section_title
;Anomeric effect and hydrogen-bonded supramolecular motif in
 5-(3-fluoro-4-methoxyphenyl)-1-[(3-fluoro-4-methoxyphenyl)aminomethyl]-1,3,5-triazinane-2-thione
;
_journal_coeditor_code           DN3126
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o558
_journal_page_last               o561
_journal_paper_doi               10.1107/S0108270109038487
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H20 F2 N4 O2 S'
_chemical_formula_moiety         'C18 H20 F2 N4 O2 S'
_chemical_formula_sum            'C18 H20 F2 N4 O2 S'
_chemical_formula_weight         394.44
_chemical_name_systematic
5-(3-fluoro-4-methoxyphenyl)-1-[(3-fluoro-4-methoxyphenyl)aminomethyl]-1,3,5-triazinane-2-thione
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                106.6930(10)
_cell_angle_beta                 102.3620(10)
_cell_angle_gamma                103.7150(10)
_cell_formula_units_Z            2
_cell_length_a                   6.6019(8)
_cell_length_b                   11.1195(13)
_cell_length_c                   13.9076(17)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.99
_cell_volume                     905.31(19)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6772
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9510
_exptl_absorpt_correction_T_min  0.9348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0380
_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)+(0.0413P)²+0.2709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                2683
_reflns_number_total             3341
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3126.cif
_cod_data_source_block           I
_cod_database_code               2017375
_cod_database_fobs_code          2017375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.23235(9) 0.30856(5) -0.04874(4) 0.05375(16) Uani d . 1 . .
F F1 -0.62384(18) -0.05474(14) 0.24186(11) 0.0721(4) Uani d . 1 . .
F F2 0.0469(2) 0.32005(16) 0.50105(12) 0.0902(5) Uani d . 1 . .
O O1 -0.2537(2) -0.09836(15) 0.30595(13) 0.0663(4) Uani d . 1 . .
O O2 0.3728(2) 0.22553(15) 0.50330(11) 0.0612(4) Uani d . 1 . .
N N1 0.1966(3) 0.53756(15) 0.26436(12) 0.0518(4) Uani d . 1 . .
N N2 0.3653(3) 0.51616(16) 0.12691(12) 0.0559(4) Uani d . 1 . .
H H2 0.4816 0.5355 0.1084 0.067 Uiso calc R 1 . .
N N3 0.0144(2) 0.38053(15) 0.08834(11) 0.0459(4) Uani d . 1 . .
N N4 -0.3316(3) 0.22545(17) 0.06919(14) 0.0581(4) Uani d . 1 . .
H H4 -0.4429 0.2533 0.0664 0.070 Uiso calc R 1 . .
C C1 0.3618(4) 0.60429(19) 0.22739(16) 0.0618(6) Uani d . 1 . .
H H1A 0.5039 0.6328 0.2794 0.074 Uiso calc R 1 . .
H H1B 0.3319 0.6823 0.2183 0.074 Uiso calc R 1 . .
C C2 -0.0081(3) 0.4776(2) 0.18020(15) 0.0545(5) Uani d . 1 . .
H H2A -0.0526 0.5459 0.1595 0.065 Uiso calc R 1 . .
H H2B -0.1205 0.4336 0.2048 0.065 Uiso calc R 1 . .
C C3 0.1997(3) 0.40753(18) 0.06202(14) 0.0443(4) Uani d . 1 . .
C C4 -0.1813(3) 0.2665(2) 0.01638(15) 0.0553(5) Uani d . 1 . .
H H4A -0.2550 0.2913 -0.0395 0.066 Uiso calc R 1 . .
H H4B -0.1342 0.1927 -0.0158 0.066 Uiso calc R 1 . .
C C5 -0.2572(3) -0.01931(18) 0.24626(15) 0.0463(4) Uani d . 1 . .
C C6 -0.4521(3) 0.00398(18) 0.21346(15) 0.0467(4) Uani d . 1 . .
C C7 -0.4804(3) 0.08152(18) 0.15476(14) 0.0474(4) Uani d . 1 . .
H H7 -0.6153 0.0940 0.1346 0.057 Uiso calc R 1 . .
C C8 -0.3054(3) 0.14196(17) 0.12523(14) 0.0437(4) Uani d . 1 . .
C C9 -0.1091(3) 0.11870(19) 0.15612(16) 0.0500(5) Uani d . 1 . .
H H9 0.0092 0.1569 0.1365 0.060 Uiso calc R 1 . .
C C10 -0.0860(3) 0.03925(18) 0.21584(16) 0.0506(5) Uani d . 1 . .
H H10 0.0478 0.0253 0.2357 0.061 Uiso calc R 1 . .
C C11 -0.0492(4) -0.1131(2) 0.34785(19) 0.0692(6) Uani d . 1 . .
H H11A -0.0010 -0.1573 0.2912 0.104 Uiso calc R 1 . .
H H11B -0.0647 -0.1647 0.3922 0.104 Uiso calc R 1 . .
H H11C 0.0566 -0.0274 0.3885 0.104 Uiso calc R 1 . .
C C12 0.2519(3) 0.45361(17) 0.32008(13) 0.0441(4) Uani d . 1 . .
C C13 0.1229(3) 0.42315(19) 0.38210(15) 0.0517(5) Uani d . 1 . .
H H13 0.0047 0.4544 0.3846 0.062 Uiso calc R 1 . .
C C14 0.1714(3) 0.3471(2) 0.43909(16) 0.0529(5) Uani d . 1 . .
C C15 0.3456(3) 0.29858(18) 0.44038(14) 0.0464(4) Uani d . 1 . .
C C16 0.4728(3) 0.3289(2) 0.37880(15) 0.0507(5) Uani d . 1 . .
H H16 0.5919 0.2982 0.3774 0.061 Uiso calc R 1 . .
C C17 0.4253(3) 0.40515(19) 0.31837(14) 0.0506(5) Uani d . 1 . .
H H17 0.5117 0.4235 0.2764 0.061 Uiso calc R 1 . .
C C18 0.5573(4) 0.1807(2) 0.51179(18) 0.0651(6) Uani d . 1 . .
H H18A 0.5484 0.1226 0.4438 0.098 Uiso calc R 1 . .
H H18B 0.5601 0.1338 0.5600 0.098 Uiso calc R 1 . .
H H18C 0.6884 0.2553 0.5373 0.098 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'
S S 0.1246 0.1234 '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
O1 C5 C10 . . 126.63(17) n
O1 C5 C6 . . 116.69(16) n
C10 C5 C6 . . 116.67(16) n
F1 C6 C7 . . 119.09(16) n
F1 C6 C5 . . 117.33(16) n
C7 C6 C5 . . 123.59(16) n
C6 C7 C8 . . 119.47(17) n
C6 C7 H7 . . 120.3 n
C8 C7 H7 . . 120.3 n
C9 C8 N4 . . 122.55(16) n
C9 C8 C7 . . 117.96(16) n
N4 C8 C7 . . 119.47(16) n
C8 C9 C10 . . 121.03(17) n
C8 C9 H9 . . 119.5 n
C10 C9 H9 . . 119.5 n
C5 C10 C9 . . 121.27(17) n
C5 C10 H10 . . 119.4 n
C9 C10 H10 . . 119.4 n
O1 C11 H11A . . 109.5 n
O1 C11 H11B . . 109.5 n
H11A C11 H11B . . 109.5 n
O1 C11 H11C . . 109.5 n
H11A C11 H11C . . 109.5 n
H11B C11 H11C . . 109.5 n
N4 C4 N3 . . 112.62(16) y
N4 C4 H4A . . 109.1 n
N3 C4 H4A . . 109.1 n
N4 C4 H4B . . 109.1 n
N3 C4 H4B . . 109.1 n
H4A C4 H4B . . 107.8 n
N2 C3 N3 . . 117.87(17) n
N2 C3 S1 . . 119.38(15) n
N3 C3 S1 . . 122.75(15) n
N1 C1 N2 . . 110.71(16) y
N1 C1 H1A . . 109.5 n
N2 C1 H1A . . 109.5 n
N1 C1 H1B . . 109.5 n
N2 C1 H1B . . 109.5 n
H1A C1 H1B . . 108.1 n
N1 C2 N3 . . 110.60(16) y
N1 C2 H2A . . 109.5 n
N3 C2 H2A . . 109.5 n
N1 C2 H2B . . 109.5 n
N3 C2 H2B . . 109.5 n
H2A C2 H2B . . 108.1 n
C17 C12 C13 . . 118.53(17) n
C17 C12 N1 . . 124.77(16) n
C13 C12 N1 . . 116.67(17) n
C14 C13 C12 . . 119.29(18) n
C14 C13 H13 . . 120.4 n
C12 C13 H13 . . 120.4 n
F2 C14 C13 . . 118.84(17) n
F2 C14 C15 . . 117.45(16) n
C13 C14 C15 . . 123.68(17) n
O2 C15 C16 . . 127.08(18) n
O2 C15 C14 . . 116.07(16) n
C16 C15 C14 . . 116.85(17) n
C15 C16 C17 . . 120.75(18) n
C15 C16 H16 . . 119.6 n
C17 C16 H16 . . 119.6 n
C12 C17 C16 . . 120.89(17) n
C12 C17 H17 . . 119.6 n
C16 C17 H17 . . 119.6 n
O2 C18 H18A . . 109.5 n
O2 C18 H18B . . 109.5 n
H18A C18 H18B . . 109.5 n
O2 C18 H18C . . 109.5 n
H18A C18 H18C . . 109.5 n
H18B C18 H18C . . 109.5 n
C8 N4 C4 . . 122.49(16) n
C8 N4 H4 . . 118.8 n
C4 N4 H4 . . 118.8 n
C3 N3 C2 . . 119.30(16) n
C3 N3 C4 . . 120.73(16) n
C2 N3 C4 . . 119.12(16) n
C12 N1 C1 . . 117.62(17) n
C12 N1 C2 . . 114.78(15) n
C1 N1 C2 . . 109.06(15) n
C3 N2 C1 . . 124.40(17) n
C3 N2 H2 . . 117.8 n
C1 N2 H2 . . 117.8 n
C5 O1 C11 . . 117.01(15) n
C15 O2 C18 . . 117.81(16) n
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
C5 O1 . 1.372(2) n
C5 C10 . 1.376(2) n
C5 C6 . 1.380(3) n
C6 F1 . 1.363(2) n
C6 C7 . 1.364(3) n
C7 C8 . 1.396(3) n
C7 H7 . 0.9300 n
C8 C9 . 1.384(2) n
C8 N4 . 1.390(2) n
C9 C10 . 1.387(2) n
C9 H9 . 0.9300 n
C10 H10 . 0.9300 n
C11 O1 . 1.419(2) n
C11 H11A . 0.9600 n
C11 H11B . 0.9600 n
C11 H11C . 0.9600 n
C4 N4 . 1.422(2) y
C4 N3 . 1.490(2) y
C4 H4A . 0.9700 n
C4 H4B . 0.9700 n
C3 N2 . 1.339(2) y
C3 N3 . 1.342(2) n
C3 S1 . 1.7063(19) n
C1 N1 . 1.442(2) y
C1 N2 . 1.467(2) y
C1 H1A . 0.9700 n
C1 H1B . 0.9700 n
C2 N1 . 1.445(3) y
C2 N3 . 1.478(2) y
C2 H2A . 0.9700 n
C2 H2B . 0.9700 n
C12 C17 . 1.377(3) n
C12 C13 . 1.389(2) n
C12 N1 . 1.436(2) n
C13 C14 . 1.360(3) n
C13 H13 . 0.9300 n
C14 F2 . 1.358(2) n
C14 C15 . 1.380(3) n
C15 O2 . 1.367(2) n
C15 C16 . 1.376(3) n
C16 C17 . 1.395(3) n
C16 H16 . 0.9300 n
C17 H17 . 0.9300 n
C18 O2 . 1.416(2) n
C18 H18A . 0.9600 n
C18 H18B . 0.9600 n
C18 H18C . 0.9600 n
N4 H4 . 0.8600 n
N2 H2 . 0.8600 n
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
N2 H2 S1 2_665 0.86 2.68 3.469(2) 152.3
N4 H4 S1 1_455 0.86 2.69 3.456(2) 148.4
C10 H10 F1 1_655 0.93 2.53 3.434(3) 165.0
C11 H11B F2 2_556 0.96 2.59 3.535(3) 168.6
C18 H18C F2 1_655 0.96 2.51 3.292(3) 139.0
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
O1 C5 C6 F1 . . . . -0.9(3) n
C10 C5 C6 F1 . . . . 179.19(17) n
O1 C5 C6 C7 . . . . 179.25(17) n
C10 C5 C6 C7 . . . . -0.7(3) n
F1 C6 C7 C8 . . . . -179.94(16) n
C5 C6 C7 C8 . . . . -0.1(3) n
C6 C7 C8 C9 . . . . 0.9(3) n
C6 C7 C8 N4 . . . . -177.31(17) n
N4 C8 C9 C10 . . . . 177.22(18) n
C7 C8 C9 C10 . . . . -0.9(3) n
O1 C5 C10 C9 . . . . -179.27(19) n
C6 C5 C10 C9 . . . . 0.7(3) n
C8 C9 C10 C5 . . . . 0.1(3) n
C17 C12 C13 C14 . . . . 0.1(3) n
N1 C12 C13 C14 . . . . -178.13(18) n
C12 C13 C14 F2 . . . . 178.74(18) n
C12 C13 C14 C15 . . . . 0.8(3) n
F2 C14 C15 O2 . . . . 1.1(3) n
C13 C14 C15 O2 . . . . 178.99(19) n
F2 C14 C15 C16 . . . . -178.79(18) n
C13 C14 C15 C16 . . . . -0.9(3) n
O2 C15 C16 C17 . . . . -179.90(18) n
C14 C15 C16 C17 . . . . -0.1(3) n
C13 C12 C17 C16 . . . . -1.0(3) n
N1 C12 C17 C16 . . . . 177.09(17) n
C15 C16 C17 C12 . . . . 1.0(3) n
C9 C8 N4 C4 . . . . 16.4(3) n
C7 C8 N4 C4 . . . . -165.55(18) n
N3 C4 N4 C8 . . . . -82.2(2) n
N2 C3 N3 C2 . . . . 6.5(2) n
S1 C3 N3 C2 . . . . -174.36(12) n
N2 C3 N3 C4 . . . . 175.87(15) n
S1 C3 N3 C4 . . . . -5.0(2) n
N1 C2 N3 C3 . . . . -38.6(2) n
N1 C2 N3 C4 . . . . 151.90(15) n
N4 C4 N3 C3 . . . . 159.98(16) n
N4 C4 N3 C2 . . . . -30.6(2) n
C17 C12 N1 C1 . . . . -17.3(3) n
C13 C12 N1 C1 . . . . 160.84(17) n
C17 C12 N1 C2 . . . . 113.1(2) n
C13 C12 N1 C2 . . . . -68.8(2) n
N2 C1 N1 C12 . . . . 82.6(2) n
N2 C1 N1 C2 . . . . -50.3(2) n
N3 C2 N1 C12 . . . . -74.42(19) n
N3 C2 N1 C1 . . . . 59.98(19) n
N3 C3 N2 C1 . . . . 3.0(3) n
S1 C3 N2 C1 . . . . -176.13(15) n
N1 C1 N2 C3 . . . . 19.9(3) n
C10 C5 O1 C11 . . . . 5.4(3) n
C6 C5 O1 C11 . . . . -174.51(19) n
C16 C15 O2 C18 . . . . 3.6(3) n
C14 C15 O2 C18 . . . . -176.26(18) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726538
