#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/76/2017650.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_2017650
loop_
_publ_author_name
'Fatila, Elisabeth M.'
'Jennings, Michael C.'
'Goodreid, Jordan'
'Preuss, Kathryn E.'
_publ_section_title
;
 A third polymorph of 4-(2,6-difluorophenyl)-1,2,3,5-dithiadiazolyl
;
_journal_coeditor_code           GG3222
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o260
_journal_page_last               o264
_journal_paper_doi               10.1107/S0108270110014393
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H3 F2 N2 S2'
_chemical_formula_moiety         'C7 H3 F2 N2 S2'
_chemical_formula_sum            'C7 H3 F2 N2 S2'
_chemical_formula_weight         217.23
_chemical_name_systematic
;
4-(2,6-difluorophenyl)-1,2,3,5-dithiadiazolyl
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.846(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.3839(5)
_cell_length_b                   7.9745(3)
_cell_length_c                   20.5463(8)
_cell_measurement_reflns_used    6691
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.04
_cell_volume                     1600.32(12)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_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  0.085
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            141999
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.9685
_exptl_absorpt_correction_T_min  0.7827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            blue-red
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.492
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0389
_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)+(0.0459P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                2045
_reflns_number_total             2831
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3222.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017650
_cod_database_fobs_code          2017650
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'
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 0.01436(8) 0.99771(9) 0.26038(4) 0.0214(2) Uani d . 1 . .
S S2 0.18635(8) 1.15194(9) 0.28564(4) 0.0214(2) Uani d . 1 . .
F F12 0.42018(15) 0.74548(19) 0.42224(8) 0.0221(4) Uani d . 1 . .
F F13 0.24386(16) 0.6340(2) 0.18422(8) 0.0255(4) Uani d . 1 . .
N N3 0.2970(2) 0.9981(3) 0.30063(12) 0.0186(6) Uani d . 1 . .
N N5 0.1030(2) 0.8243(3) 0.27239(13) 0.0202(6) Uani d . 1 . .
C C4 0.2381(3) 0.8462(4) 0.29171(14) 0.0180(7) Uani d . 1 . .
C C6 0.3274(3) 0.6950(4) 0.30268(15) 0.0166(7) Uani d . 1 . .
C C7 0.4155(3) 0.6476(4) 0.36723(15) 0.0182(7) Uani d . 1 . .
C C8 0.4960(3) 0.5079(4) 0.37855(16) 0.0198(7) Uani d . 1 . .
H H8A 0.5535 0.4787 0.4239 0.024 Uiso calc R 1 . .
C C9 0.4918(3) 0.4096(4) 0.32219(16) 0.0222(7) Uani d . 1 . .
H H9A 0.5478 0.3125 0.3288 0.027 Uiso calc R 1 . .
C C10 0.4069(3) 0.4520(4) 0.25647(16) 0.0213(7) Uani d . 1 . .
H H10A 0.4039 0.3853 0.2177 0.026 Uiso calc R 1 . .
C C11 0.3270(3) 0.5923(4) 0.24851(15) 0.0192(7) Uani d . 1 . .
S S21 0.32455(7) 1.11148(10) 0.47806(4) 0.0215(2) Uani d . 1 . .
S S22 0.40824(8) 0.95293(10) 0.56339(4) 0.0206(2) Uani d . 1 . .
F F32 0.23937(16) 0.50462(19) 0.45518(9) 0.0278(5) Uani d . 1 . .
F F33 -0.08452(16) 0.9331(2) 0.43019(9) 0.0270(4) Uani d . 1 . .
N N23 0.2892(2) 0.8106(3) 0.53573(12) 0.0186(6) Uani d . 1 . .
N N25 0.1958(2) 0.9884(3) 0.43985(12) 0.0186(6) Uani d . 1 . .
C C24 0.1947(3) 0.8477(4) 0.47445(15) 0.0188(7) Uani d . 1 . .
C C26 0.0835(3) 0.7248(4) 0.44455(14) 0.0172(7) Uani d . 1 . .
C C27 0.1071(3) 0.5558(4) 0.43745(15) 0.0203(7) Uani d . 1 . .
C C28 0.0059(3) 0.4380(4) 0.41340(15) 0.0233(7) Uani d . 1 . .
H H28A 0.0273 0.3234 0.4096 0.028 Uiso calc R 1 . .
C C29 -0.1287(3) 0.4917(4) 0.39476(15) 0.0258(8) Uani d . 1 . .
H H29A -0.2010 0.4126 0.3782 0.031 Uiso calc R 1 . .
C C30 -0.1592(3) 0.6584(4) 0.39992(15) 0.0240(8) Uani d . 1 . .
H H30A -0.2515 0.6950 0.3869 0.029 Uiso calc R 1 . .
C C31 -0.0535(3) 0.7701(4) 0.42415(15) 0.0204(7) 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'
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'
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
N5 S1 S2 . . 94.07(9) ?
N3 S2 S1 . . 95.26(9) ?
C4 N3 S2 . . 113.1(2) ?
C4 N5 S1 . . 114.6(2) ?
N5 C4 N3 . . 123.0(3) ?
N5 C4 C6 . . 118.5(3) ?
N3 C4 C6 . . 118.6(2) ?
C11 C6 C7 . . 115.5(3) ?
C11 C6 C4 . . 121.8(3) ?
C7 C6 C4 . . 122.7(3) ?
F12 C7 C8 . . 118.7(3) ?
F12 C7 C6 . . 117.7(3) ?
C8 C7 C6 . . 123.6(3) ?
C7 C8 C9 . . 118.4(3) ?
C7 C8 H8A . . 120.8 ?
C9 C8 H8A . . 120.8 ?
C10 C9 C8 . . 120.4(3) ?
C10 C9 H9A . . 119.8 ?
C8 C9 H9A . . 119.8 ?
C11 C10 C9 . . 118.5(3) ?
C11 C10 H10A . . 120.8 ?
C9 C10 H10A . . 120.8 ?
F13 C11 C10 . . 118.6(3) ?
F13 C11 C6 . . 117.9(3) ?
C10 C11 C6 . . 123.6(3) ?
N25 S21 S22 . . 94.53(9) ?
N23 S22 S21 . . 94.50(9) ?
C24 N23 S22 . . 113.6(2) ?
C24 N25 S21 . . 113.9(2) ?
N25 C24 N23 . . 123.5(3) ?
N25 C24 C26 . . 118.9(3) ?
N23 C24 C26 . . 117.6(3) ?
C27 C26 C31 . . 114.9(3) ?
C27 C26 C24 . . 123.2(3) ?
C31 C26 C24 . . 121.9(3) ?
F32 C27 C28 . . 118.2(3) ?
F32 C27 C26 . . 117.5(3) ?
C28 C27 C26 . . 124.2(3) ?
C27 C28 C29 . . 117.8(3) ?
C27 C28 H28A . . 121.1 ?
C29 C28 H28A . . 121.1 ?
C30 C29 C28 . . 120.8(3) ?
C30 C29 H29A . . 119.6 ?
C28 C29 H29A . . 119.6 ?
C31 C30 C29 . . 118.6(3) ?
C31 C30 H30A . . 120.7 ?
C29 C30 H30A . . 120.7 ?
F33 C31 C30 . . 118.1(3) ?
F33 C31 C26 . . 118.3(3) ?
C30 C31 C26 . . 123.6(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
S1 N5 . 1.633(2) ?
S1 S2 . 2.0838(10) ?
S2 N3 . 1.637(2) ?
F12 C7 . 1.361(3) ?
F13 C11 . 1.352(3) ?
N3 C4 . 1.341(3) ?
N5 C4 . 1.333(3) ?
C4 C6 . 1.491(4) ?
C6 C11 . 1.381(4) ?
C6 C7 . 1.384(4) ?
C7 C8 . 1.364(4) ?
C8 C9 . 1.387(4) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.381(4) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.369(4) ?
C10 H10A . 0.9500 ?
S21 N25 . 1.629(2) ?
S21 S22 . 2.0960(11) ?
S22 N23 . 1.632(2) ?
F32 C27 . 1.359(3) ?
F33 C31 . 1.355(3) ?
N23 C24 . 1.341(3) ?
N25 C24 . 1.330(3) ?
C24 C26 . 1.480(4) ?
C26 C27 . 1.386(4) ?
C26 C31 . 1.387(4) ?
C27 C28 . 1.370(4) ?
C28 C29 . 1.386(4) ?
C28 H28A . 0.9500 ?
C29 C30 . 1.379(4) ?
C29 H29A . 0.9500 ?
C30 C31 . 1.369(4) ?
C30 H30A . 0.9500 ?
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
N5 S1 S2 N3 . . . . 0.18(13) ?
S1 S2 N3 C4 . . . . -0.2(2) ?
S2 S1 N5 C4 . . . . -0.1(2) ?
S1 N5 C4 N3 . . . . 0.0(4) ?
S1 N5 C4 C6 . . . . -178.9(2) ?
S2 N3 C4 N5 . . . . 0.2(4) ?
S2 N3 C4 C6 . . . . 179.1(2) ?
N5 C4 C6 C11 . . . . 67.7(4) ?
N3 C4 C6 C11 . . . . -111.2(3) ?
N5 C4 C6 C7 . . . . -112.1(3) ?
N3 C4 C6 C7 . . . . 69.0(4) ?
C11 C6 C7 F12 . . . . 179.6(2) ?
C4 C6 C7 F12 . . . . -0.6(4) ?
C11 C6 C7 C8 . . . . -1.2(4) ?
C4 C6 C7 C8 . . . . 178.6(3) ?
F12 C7 C8 C9 . . . . -179.3(3) ?
C6 C7 C8 C9 . . . . 1.4(5) ?
C7 C8 C9 C10 . . . . -0.7(4) ?
C8 C9 C10 C11 . . . . -0.3(4) ?
C9 C10 C11 F13 . . . . 179.9(3) ?
C9 C10 C11 C6 . . . . 0.5(5) ?
C7 C6 C11 F13 . . . . -179.3(2) ?
C4 C6 C11 F13 . . . . 0.9(4) ?
C7 C6 C11 C10 . . . . 0.1(4) ?
C4 C6 C11 C10 . . . . -179.7(3) ?
N25 S21 S22 N23 . . . . -0.22(12) ?
S21 S22 N23 C24 . . . . 0.7(2) ?
S22 S21 N25 C24 . . . . -0.3(2) ?
S21 N25 C24 N23 . . . . 1.0(4) ?
S21 N25 C24 C26 . . . . -179.3(2) ?
S22 N23 C24 N25 . . . . -1.2(4) ?
S22 N23 C24 C26 . . . . 179.1(2) ?
N25 C24 C26 C27 . . . . 129.4(3) ?
N23 C24 C26 C27 . . . . -50.9(4) ?
N25 C24 C26 C31 . . . . -53.4(4) ?
N23 C24 C26 C31 . . . . 126.3(3) ?
C31 C26 C27 F32 . . . . 178.6(2) ?
C24 C26 C27 F32 . . . . -4.1(4) ?
C31 C26 C27 C28 . . . . -1.0(4) ?
C24 C26 C27 C28 . . . . 176.4(3) ?
F32 C27 C28 C29 . . . . -179.3(2) ?
C26 C27 C28 C29 . . . . 0.2(4) ?
C27 C28 C29 C30 . . . . 0.4(4) ?
C28 C29 C30 C31 . . . . -0.3(5) ?
C29 C30 C31 F33 . . . . -178.8(3) ?
C29 C30 C31 C26 . . . . -0.6(5) ?
C27 C26 C31 F33 . . . . 179.4(2) ?
C24 C26 C31 F33 . . . . 2.0(4) ?
C27 C26 C31 C30 . . . . 1.2(4) ?
C24 C26 C31 C30 . . . . -176.2(3) ?
