##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2015-03-20
_journal_date_accepted     2015-03-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      5
_journal_page_first     o268
_journal_page_last     o269
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015005836
_journal_coeditor_code     HB7389
_publ_contact_author_name
;
 'Noor Shahina Begum'
;
_publ_contact_author_address
;
 Department of Studies in Chemistry
 Central College Campus
 Bangalore University
 Bangalore,560001
 India
;
_publ_contact_author_email     'noorsb@rediffmail.com'
_publ_contact_author_fax     '(91) 80 2296 1331'
_publ_contact_author_phone     '(91) 80 2296 1344'
_publ_section_title
;\
Crystal structure of ethyl
6-(2-fluorophenyl)-4-hydroxy-2-sulfanylidene-4-trifluoromethyl-1,3-\
diazinane-5-carboxylate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Krishnamurthy, M. S.'
;
 Department of Studies in Chemistry,
 Central College Campus,
 Bangalore University,
 Bangalore 560 001,
 Karnataka
 India
;
    'Noor Shahina Begum'
;
 Department of Studies in Chemistry,
 Central College Campus,
 Bangalore University,
 Bangalore 560 001,
 Karnataka
 India
;
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 1055499'
_chemical_name_systematic
;
Ethyl 6-(2-fluorophenyl)-4-hydroxy-2-sulfanylidene-4-trifluoromethyl-
1,3-diazinane-5-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 F4 N2 O3 S'
_chemical_formula_sum     'C14 H14 F4 N2 O3 S'
_chemical_formula_iupac     'C14 H14 F4 N2 O3 S'
_chemical_formula_weight     366.33
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.937(3)
_cell_length_b     9.934(3)
_cell_length_c     14.629(4)
_cell_angle_alpha     90.00
_cell_angle_beta     108.239(5)
_cell_angle_gamma     90.00
_cell_volume     1509.7(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2646
_cell_measurement_theta_min     1.96
_cell_measurement_theta_max     25.00
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.612
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     752
_exptl_absorpt_coefficient_mu     0.277
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 1998)
;
_exptl_absorpt_correction_T_min     0.9519
_exptl_absorpt_correction_T_max     0.9571
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7619
_diffrn_reflns_av_R_equivalents     0.0341
_diffrn_reflns_av_sigmaI/netI     0.0401
_diffrn_reflns_theta_min     1.96
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2646
_reflns_number_gt     2138
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0573
_refine_ls_R_factor_gt     0.0459
_refine_ls_wR_factor_gt     0.1268
_refine_ls_wR_factor_ref     0.1412
_refine_ls_goodness_of_fit_ref     1.032
_refine_ls_restrained_S_all     1.032
_refine_ls_number_reflns     2646
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0939P)²+0.0341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.635
_refine_diff_density_min     -0.286
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'F' 'F' 0.0171 0.0103
                         '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'
_computing_data_collection
;
SMART (Bruker,1998)
;
_computing_cell_refinement
;
SAINT-Plus (Bruker, 1998)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 1998)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin et al.,
1996)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.09623(6) 0.40020(7) 0.12780(4) 0.0190(2) Uani d . 1 1 . .
    O O1 -0.35850(17) 0.71225(18) 0.25205(13) 0.0243(5) Uani d . 1 1 . .
    O O2 -0.44764(17) 0.50537(18) 0.22450(13) 0.0214(4) Uani d . 1 1 . .
    O O3 -0.18273(16) 0.75721(18) 0.15250(12) 0.0194(4) Uani d . 1 1 . .
    H H3 -0.2203 0.7777 0.1926 0.029 Uiso calc R 1 1 . .
    N N1 -0.10705(19) 0.5616(2) 0.09977(14) 0.0177(5) Uani d . 1 1 . .
    H H1 -0.0968 0.5790 0.0436 0.021 Uiso calc R 1 1 . .
    N N2 -0.0313(2) 0.4589(2) 0.24785(14) 0.0178(5) Uani d . 1 1 . .
    H H2 0.0244 0.4048 0.2875 0.021 Uiso calc R 1 1 . .
    F F1 -0.36294(14) 0.50800(15) -0.00967(10) 0.0242(4) Uani d . 1 1 . .
    F F2 -0.29456(14) 0.70124(16) -0.04041(10) 0.0238(4) Uani d . 1 1 . .
    F F3 -0.42992(13) 0.68945(15) 0.03915(10) 0.0225(4) Uani d . 1 1 . .
    F F4 -0.18118(15) 0.23990(15) 0.27621(10) 0.0270(4) Uani d . 1 1 . .
    C C1 -0.3263(2) 0.6310(3) 0.02677(18) 0.0183(6) Uani d . 1 1 . .
    C C2 -0.0206(2) 0.4780(2) 0.16074(18) 0.0165(6) Uani d . 1 1 . .
    C C3 -0.3585(2) 0.5968(3) 0.22634(18) 0.0189(6) Uani d . 1 1 . .
    C C6 -0.1299(2) 0.5223(3) 0.28213(17) 0.0182(6) Uani d . 1 1 . .
    H H6 -0.0996 0.6145 0.3062 0.022 Uiso calc R 1 1 . .
    C C5 -0.2516(2) 0.5364(3) 0.19469(17) 0.0164(6) Uani d . 1 1 . .
    H H5 -0.2787 0.4454 0.1664 0.020 Uiso calc R 1 1 . .
    C C4 -0.2143(2) 0.6238(3) 0.12085(18) 0.0163(6) Uani d . 1 1 . .
    C C7 -0.5546(3) 0.5477(3) 0.2590(2) 0.0270(7) Uani d . 1 1 . .
    H H7A -0.6337 0.4981 0.2234 0.032 Uiso calc R 1 1 . .
    H H7B -0.5711 0.6451 0.2465 0.032 Uiso calc R 1 1 . .
    C C8 -0.5230(3) 0.5208(3) 0.3643(2) 0.0334(7) Uani d . 1 1 . .
    H H8A -0.5017 0.4254 0.3770 0.050 Uiso calc R 1 1 . .
    H H8B -0.5975 0.5433 0.3851 0.050 Uiso calc R 1 1 . .
    H H8C -0.4493 0.5761 0.3999 0.050 Uiso calc R 1 1 . .
    C C9 -0.1537(2) 0.4440(3) 0.36335(17) 0.0163(6) Uani d . 1 1 . .
    C C10 -0.1553(2) 0.5097(3) 0.44637(17) 0.0182(6) Uani d . 1 1 . .
    H H10 -0.1368 0.6033 0.4530 0.022 Uiso calc R 1 1 . .
    C C11 -0.1832(2) 0.4416(3) 0.51975(18) 0.0210(6) Uani d . 1 1 . .
    H H11 -0.1870 0.4889 0.5752 0.025 Uiso calc R 1 1 . .
    C C12 -0.2054(2) 0.3050(3) 0.51222(19) 0.0235(6) Uani d . 1 1 . .
    H H12 -0.2225 0.2579 0.5634 0.028 Uiso calc R 1 1 . .
    C C13 -0.2031(2) 0.2362(3) 0.43111(17) 0.0214(6) Uani d . 1 1 . .
    H H13 -0.2176 0.1418 0.4259 0.026 Uiso calc R 1 1 . .
    C C14 -0.1794(2) 0.3073(3) 0.35795(18) 0.0199(6) Uani d . 1 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 C2 . 1.688(3) ?
    O1 C3 . 1.207(3) ?
    O2 C3 . 1.327(3) ?
    O2 C7 . 1.473(3) ?
    O3 C4 . 1.411(3) ?
    O3 H3 . 0.8400 ?
    N1 C2 . 1.361(3) ?
    N1 C4 . 1.442(3) ?
    N1 H1 . 0.8800 ?
    N2 C2 . 1.329(3) ?
    N2 C6 . 1.466(3) ?
    N2 H2 . 0.8800 ?
    F1 C1 . 1.343(3) ?
    F2 C1 . 1.337(3) ?
    F3 C1 . 1.335(3) ?
    F4 C14 . 1.365(3) ?
    C1 C4 . 1.531(3) ?
    C3 C5 . 1.510(3) ?
    C6 C9 . 1.509(3) ?
    C6 C5 . 1.537(3) ?
    C6 H6 . 1.0000 ?
    C5 C4 . 1.537(3) ?
    C5 H5 . 1.0000 ?
    C7 C8 . 1.494(4) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 C10 . 1.384(3) ?
    C9 C14 . 1.384(4) ?
    C10 C11 . 1.381(4) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.377(4) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.377(4) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.373(4) ?
    C13 H13 . 0.9500 ?
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 O2 C7 . . 117.0(2) ?
    C4 O3 H3 . . 109.5 ?
    C2 N1 C4 . . 124.5(2) ?
    C2 N1 H1 . . 117.8 ?
    C4 N1 H1 . . 117.8 ?
    C2 N2 C6 . . 124.1(2) ?
    C2 N2 H2 . . 117.9 ?
    C6 N2 H2 . . 117.9 ?
    F3 C1 F2 . . 107.4(2) ?
    F3 C1 F1 . . 106.8(2) ?
    F2 C1 F1 . . 107.3(2) ?
    F3 C1 C4 . . 111.9(2) ?
    F2 C1 C4 . . 111.5(2) ?
    F1 C1 C4 . . 111.7(2) ?
    N2 C2 N1 . . 117.7(2) ?
    N2 C2 S1 . . 120.65(19) ?
    N1 C2 S1 . . 121.70(19) ?
    O1 C3 O2 . . 125.8(2) ?
    O1 C3 C5 . . 123.3(2) ?
    O2 C3 C5 . . 110.9(2) ?
    N2 C6 C9 . . 112.0(2) ?
    N2 C6 C5 . . 107.03(19) ?
    C9 C6 C5 . . 112.6(2) ?
    N2 C6 H6 . . 108.4 ?
    C9 C6 H6 . . 108.4 ?
    C5 C6 H6 . . 108.4 ?
    C3 C5 C6 . . 109.46(19) ?
    C3 C5 C4 . . 113.1(2) ?
    C6 C5 C4 . . 106.6(2) ?
    C3 C5 H5 . . 109.2 ?
    C6 C5 H5 . . 109.2 ?
    C4 C5 H5 . . 109.2 ?
    O3 C4 N1 . . 109.9(2) ?
    O3 C4 C1 . . 107.2(2) ?
    N1 C4 C1 . . 107.66(19) ?
    O3 C4 C5 . . 113.1(2) ?
    N1 C4 C5 . . 108.7(2) ?
    C1 C4 C5 . . 110.1(2) ?
    O2 C7 C8 . . 110.5(2) ?
    O2 C7 H7A . . 109.6 ?
    C8 C7 H7A . . 109.6 ?
    O2 C7 H7B . . 109.6 ?
    C8 C7 H7B . . 109.6 ?
    H7A C7 H7B . . 108.1 ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C10 C9 C14 . . 117.0(2) ?
    C10 C9 C6 . . 120.0(2) ?
    C14 C9 C6 . . 122.9(2) ?
    C11 C10 C9 . . 121.2(3) ?
    C11 C10 H10 . . 119.4 ?
    C9 C10 H10 . . 119.4 ?
    C12 C11 C10 . . 119.8(2) ?
    C12 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    C13 C12 C11 . . 120.5(2) ?
    C13 C12 H12 . . 119.7 ?
    C11 C12 H12 . . 119.7 ?
    C14 C13 C12 . . 118.4(3) ?
    C14 C13 H13 . . 120.8 ?
    C12 C13 H13 . . 120.8 ?
    F4 C14 C13 . . 118.4(2) ?
    F4 C14 C9 . . 118.5(2) ?
    C13 C14 C9 . . 123.0(2) ?
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
    C6 N2 C2 N1 . . . . -0.1(4) ?
    C6 N2 C2 S1 . . . . -179.87(18) ?
    C4 N1 C2 N2 . . . . -4.3(4) ?
    C4 N1 C2 S1 . . . . 175.49(18) ?
    C7 O2 C3 O1 . . . . -1.5(4) ?
    C7 O2 C3 C5 . . . . 176.6(2) ?
    C2 N2 C6 C9 . . . . 157.1(2) ?
    C2 N2 C6 C5 . . . . 33.2(3) ?
    O1 C3 C5 C6 . . . . 69.9(3) ?
    O2 C3 C5 C6 . . . . -108.2(2) ?
    O1 C3 C5 C4 . . . . -48.7(3) ?
    O2 C3 C5 C4 . . . . 133.1(2) ?
    N2 C6 C5 C3 . . . . 178.0(2) ?
    C9 C6 C5 C3 . . . . 54.5(3) ?
    N2 C6 C5 C4 . . . . -59.4(2) ?
    C9 C6 C5 C4 . . . . 177.1(2) ?
    C2 N1 C4 O3 . . . . 98.7(3) ?
    C2 N1 C4 C1 . . . . -144.9(2) ?
    C2 N1 C4 C5 . . . . -25.5(3) ?
    F3 C1 C4 O3 . . . . -60.8(3) ?
    F2 C1 C4 O3 . . . . 59.5(3) ?
    F1 C1 C4 O3 . . . . 179.53(18) ?
    F3 C1 C4 N1 . . . . -179.01(19) ?
    F2 C1 C4 N1 . . . . -58.7(3) ?
    F1 C1 C4 N1 . . . . 61.3(3) ?
    F3 C1 C4 C5 . . . . 62.6(3) ?
    F2 C1 C4 C5 . . . . -177.09(19) ?
    F1 C1 C4 C5 . . . . -57.1(3) ?
    C3 C5 C4 O3 . . . . 54.3(3) ?
    C6 C5 C4 O3 . . . . -66.0(2) ?
    C3 C5 C4 N1 . . . . 176.62(19) ?
    C6 C5 C4 N1 . . . . 56.3(2) ?
    C3 C5 C4 C1 . . . . -65.6(3) ?
    C6 C5 C4 C1 . . . . 174.1(2) ?
    C3 O2 C7 C8 . . . . -90.8(3) ?
    N2 C6 C9 C10 . . . . 131.1(2) ?
    C5 C6 C9 C10 . . . . -108.2(3) ?
    N2 C6 C9 C14 . . . . -51.4(3) ?
    C5 C6 C9 C14 . . . . 69.3(3) ?
    C14 C9 C10 C11 . . . . -0.9(3) ?
    C6 C9 C10 C11 . . . . 176.7(2) ?
    C9 C10 C11 C12 . . . . 2.3(4) ?
    C10 C11 C12 C13 . . . . -1.6(4) ?
    C11 C12 C13 C14 . . . . -0.6(4) ?
    C12 C13 C14 F4 . . . . -178.0(2) ?
    C12 C13 C14 C9 . . . . 2.2(4) ?
    C10 C9 C14 F4 . . . . 178.7(2) ?
    C6 C9 C14 F4 . . . . 1.2(4) ?
    C10 C9 C14 C13 . . . . -1.4(4) ?
    C6 C9 C14 C13 . . . . -178.9(2) ?
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
    O3 H3 O1 . 0.84 2.07 2.787(3) 143
    C10 H10 F2 4_576 0.95 2.62 3.285(6) 128
    C13 H13 F1 4_566 0.95 2.56 3.262(8) 131
    N1 H1 S1 3_565 0.88 2.52 3.389(2) 171
    N2 H2 O3 2_545 0.88 2.23 3.079(3) 162
