#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:17:45 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180421 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/90/7209015.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_7209015
loop_
_publ_author_name
'Beldjoudi, Yassine'
'Haynes, Delia A.'
'Hayward, John J.'
'Manning, Wallace J.'
'Pratt, Douglas R.'
'Rawson, Jeremy M.'
_publ_section_title
;
 Preparation and crystal structures of the isomeric series
 4-tolyl-1,2,3,5-dithiadiazolyl, (o-MeC6H4CNSSN)2, (m-MeC6H4CNSSN)2 and
 (p-MeC6H4CNSSN)2
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1107
_journal_paper_doi               10.1039/c2ce26431e
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C8 H7 N2 S2'
_chemical_formula_sum            'C8 H7 N2 S2'
_chemical_formula_weight         195.28
_chemical_name_common            4-m-tolyl-1,2,3,5-dithiadiazolyl
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.11(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9118(12)
_cell_length_b                   13.360(3)
_cell_length_c                   10.963(2)
_cell_measurement_reflns_used    8292
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.46
_cell_volume                     835.9(3)
_computing_cell_refinement       'Bruker SAINT, v6.45a'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL XPREP'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9329
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  0.9188
_exptl_absorpt_correction_T_min  0.7702
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lathe
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0362
_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)+(0.0470P)²+0.1008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                3715
_reflns_number_total             3842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26431e.txt
_cod_data_source_block           2
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        836.0(3)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7209015
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C10 C 0.0579(4) 0.32773(15) 0.06086(19) 0.0230(4) Uani 1 1 d .
S11 S -0.27455(8) 0.44732(4) -0.01479(5) 0.02848(13) Uani 1 1 d .
N11 N -0.1463(3) 0.35845(14) 0.07945(17) 0.0262(4) Uani 1 1 d .
C11 C 0.1879(3) 0.24587(15) 0.14039(19) 0.0216(4) Uani 1 1 d .
S12 S -0.01189(10) 0.45490(4) -0.11136(5) 0.03204(14) Uani 1 1 d .
N12 N 0.1476(4) 0.36670(15) -0.02826(19) 0.0302(4) Uani 1 1 d .
C12 C 0.1095(4) 0.20853(15) 0.24025(19) 0.0229(4) Uani 1 1 d .
H12 H -0.0280 0.2357 0.2568 0.027 Uiso 1 1 calc R
C13 C 0.2293(4) 0.13191(15) 0.31661(19) 0.0252(4) Uani 1 1 d .
C14 C 0.4307(4) 0.09392(16) 0.2904(2) 0.0292(5) Uani 1 1 d .
H14 H 0.5153 0.0418 0.3416 0.035 Uiso 1 1 calc R
C15 C 0.5097(3) 0.13087(15) 0.1910(2) 0.0272(4) Uani 1 1 d .
H15 H 0.6473 0.1037 0.1744 0.033 Uiso 1 1 calc R
C16 C 0.3902(4) 0.20689(15) 0.1156(2) 0.0250(4) Uani 1 1 d .
H16 H 0.4452 0.2323 0.0476 0.030 Uiso 1 1 calc R
C17 C 0.1444(4) 0.09111(18) 0.4242(2) 0.0373(5) Uani 1 1 d .
H17A H 0.1481 0.0178 0.4224 0.056 Uiso 1 1 calc R
H17B H -0.0165 0.1137 0.4162 0.056 Uiso 1 1 calc R
H17C H 0.2460 0.1151 0.5043 0.056 Uiso 1 1 calc R
C20 C 0.2785(3) 0.50239(15) 0.27295(18) 0.0243(4) Uani 1 1 d .
S21 S -0.05752(10) 0.61175(4) 0.16397(5) 0.03303(14) Uani 1 1 d .
C21 C 0.3977(3) 0.42951(16) 0.36929(18) 0.0226(4) Uani 1 1 d .
N21 N 0.0628(3) 0.53275(15) 0.27463(17) 0.0293(4) Uani 1 1 d .
S22 S 0.23317(10) 0.61757(4) 0.08837(5) 0.03360(14) Uani 1 1 d .
N22 N 0.3860(3) 0.53651(15) 0.18870(18) 0.0304(4) Uani 1 1 d .
C22 C 0.3057(4) 0.40593(16) 0.47056(19) 0.0239(4) Uani 1 1 d .
H22 H 0.1635 0.4366 0.4758 0.029 Uiso 1 1 calc R
C23 C 0.4152(4) 0.33913(16) 0.5637(2) 0.0271(4) Uani 1 1 d .
C24 C 0.6216(4) 0.29326(18) 0.5537(2) 0.0305(5) Uani 1 1 d .
H24 H 0.6989 0.2462 0.6156 0.037 Uiso 1 1 calc R
C25 C 0.7142(4) 0.31676(18) 0.4522(2) 0.0309(5) Uani 1 1 d .
H25 H 0.8555 0.2856 0.4464 0.037 Uiso 1 1 calc R
C26 C 0.6062(4) 0.38357(16) 0.3609(2) 0.0261(4) Uani 1 1 d .
H26 H 0.6718 0.3986 0.2926 0.031 Uiso 1 1 calc R
C27 C 0.3172(4) 0.3166(2) 0.6746(2) 0.0382(5) Uani 1 1 d .
H27A H 0.4108 0.3511 0.7498 0.057 Uiso 1 1 calc R
H27B H 0.3226 0.2443 0.6899 0.057 Uiso 1 1 calc R
H27C H 0.1546 0.3398 0.6562 0.057 Uiso 1 1 calc R
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'
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
N12 C10 N11 122.5(2)
N12 C10 C11 118.37(18)
N11 C10 C11 119.07(18)
N11 S11 S12 94.14(7)
C10 N11 S11 114.60(15)
C12 C11 C16 119.9(2)
C12 C11 C10 120.05(17)
C16 C11 C10 120.00(18)
N12 S12 S11 94.55(8)
C10 N12 S12 114.16(16)
C11 C12 C13 121.09(18)
C14 C13 C12 118.18(19)
C14 C13 C17 120.64(19)
C12 C13 C17 121.18(19)
C15 C14 C13 121.00(19)
C16 C15 C14 120.56(19)
C15 C16 C11 119.2(2)
N22 C20 N21 122.2(2)
N22 C20 C21 119.86(19)
N21 C20 C21 117.92(18)
N21 S21 S22 94.29(7)
C22 C21 C26 119.1(2)
C22 C21 C20 120.47(18)
C26 C21 C20 120.45(19)
C20 N21 S21 114.73(15)
N22 S22 S21 94.34(7)
C20 N22 S22 114.39(16)
C23 C22 C21 121.93(19)
C22 C23 C24 118.43(19)
C22 C23 C27 121.3(2)
C24 C23 C27 120.2(2)
C23 C24 C25 119.7(2)
C26 C25 C24 121.6(2)
C25 C26 C21 119.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C10 N12 1.333(3)
C10 N11 1.340(3)
C10 C11 1.482(3)
S11 N11 1.6259(18)
S11 S12 2.0974(9)
C11 C12 1.388(3)
C11 C16 1.395(3)
S12 N12 1.631(2)
C12 C13 1.393(3)
C13 C14 1.392(3)
C13 C17 1.500(3)
C14 C15 1.384(3)
C15 C16 1.382(3)
C20 N22 1.331(3)
C20 N21 1.343(3)
C20 C21 1.474(3)
S21 N21 1.6254(19)
S21 S22 2.0949(9)
C21 C22 1.394(3)
C21 C26 1.401(3)
S22 N22 1.637(2)
C22 C23 1.384(3)
C23 C24 1.395(3)
C23 C27 1.507(3)
C24 C25 1.399(3)
C25 C26 1.368(3)
