#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/36/2103639.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_2103639
loop_
_publ_author_name
'Greenberg, Mark'
'Shteiman, Vitaly'
'Kaftory, Menahem'
_publ_section_title
;
 Topochemically controlled solid-state methyl rearrangement in
 thiocyanurates
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              428
_journal_page_last               434
_journal_paper_doi               10.1107/S0108768101005171
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C6 H9 N3 O2 S'
_chemical_formula_sum            'C6 H9 N3 O2 S'
_chemical_formula_weight         187.22
_chemical_name_common            9b
_chemical_name_systematic
;
 4,6-Dimethoxy-3-methyl-1,3,5-triazine-2(3H)-thion
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.99(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.657(3)
_cell_length_b                   14.361(7)
_cell_length_c                   8.433(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.7
_cell_measurement_theta_min      2.9
_cell_volume                     865.8(7)
_computing_cell_refinement       'Philips PW 110/20 (Philips, 1973)'
_computing_data_collection       'Philips PW 110/20 (Philips, 1973)'
_computing_data_reduction        'Philips PW 110/20 (Philips, 1973)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Philips PW 1100'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71070
_diffrn_reflns_av_R_equivalents  .0906
_diffrn_reflns_av_sigmaI/netI    .0708
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1730
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.84
_diffrn_standards_decay_%        4.0
_diffrn_standards_interval_time  '120 min'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .337
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             392
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .38
_exptl_crystal_size_min          .24
_refine_diff_density_max         .366
_refine_diff_density_min         -.359
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          .1344
_refine_ls_R_factor_gt           .0527
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0325P)²+2.0096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1592
_reflns_number_gt                902
_reflns_number_total             1520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            av0037.cif
_cod_data_source_block           9b
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2103639
_cod_database_fobs_code          2103639
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_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_type_symbol
S .65350(18) .12203(8) .20454(15) .0449(4) Uani d . 1 S
O1 .9234(5) -.17846(19) .1274(4) .0416(8) Uani d . 1 O
O2 .7225(4) .0157(2) -.3240(3) .0417(8) Uani d . 1 O
N1 .7932(5) -.0396(2) .1616(4) .0323(8) Uani d . 1 N
N2 .8312(5) -.0847(2) -.0980(4) .0343(8) Uani d . 1 N
N3 .6989(5) .0607(2) -.0761(4) .0334(8) Uani d . 1 N
C1 .7182(6) .0433(3) .0925(5) .0304(9) Uani d . 1 C
C2 .8461(6) -.0965(3) .0652(5) .0334(10) Uani d . 1 C
C3 .7529(6) -.0061(3) -.1635(5) .0332(10) Uani d . 1 C
C4 .9514(7) -.1985(3) .3029(5) .0464(12) Uani d . 1 C
C5 .7756(8) -.0555(4) -.4234(6) .0521(13) Uani d . 1 C
C6 .6206(7) .1495(3) -.1590(6) .0444(12) Uani d . 1 C
H4A 1.0239 -.1496 .3739 .070 Uiso calc R 1 H
H4B 1.0166 -.2566 .3350 .070 Uiso calc R 1 H
H4C .8323 -.2026 .3162 .070 Uiso calc R 1 H
H5A .9058 -.0703 -.3689 .078 Uiso calc R 1 H
H5B .7539 -.0322 -.5355 .078 Uiso calc R 1 H
H5C .7020 -.1105 -.4307 .078 Uiso calc R 1 H
H6A .6170 .1491 -.2740 .067 Uiso calc R 1 H
H6B .6977 .2000 -.0983 .067 Uiso calc R 1 H
H6C .4962 .1571 -.1587 .067 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S .0576(8) .0325(6) .0474(7) .0010(6) .0220(6) -.0064(5)
C1 .029(2) .030(2) .030(2) -.0070(17) .0084(18) -.0033(17)
C2 .035(2) .033(2) .031(2) .0013(18) .0095(19) .0051(17)
C3 .036(2) .031(2) .029(2) -.0038(19) .0066(18) .0037(17)
C4 .066(3) .038(2) .035(3) .012(2) .018(2) .012(2)
C5 .068(4) .062(3) .025(2) .004(3) .015(2) -.001(2)
C6 .055(3) .029(2) .045(3) .004(2) .013(2) .0090(19)
N1 .039(2) .0274(18) .0293(18) .0008(15) .0103(16) .0015(14)
N2 .043(2) .0300(17) .0287(18) -.0010(16) .0109(16) -.0010(15)
N3 .037(2) .0246(17) .036(2) -.0015(15) .0104(16) .0039(14)
O1 .061(2) .0325(16) .0316(16) .0079(14) .0164(15) .0058(13)
O2 .0493(19) .0486(18) .0267(16) .0000(15) .0130(14) .0038(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 '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
N1 C1 N3 117.8(4)
N1 C1 S 121.3(3)
N3 C1 S 120.9(3)
N1 C2 O1 119.7(3)
N1 C2 N2 128.4(4)
O1 C2 N2 112.0(4)
N2 C3 O2 121.6(4)
N2 C3 N3 124.3(4)
O2 C3 N3 114.1(3)
C2 N1 C1 117.1(3)
C3 N2 C2 113.5(4)
C3 N3 C1 118.9(3)
C3 N3 C6 120.3(3)
C1 N3 C6 120.9(3)
C2 O1 C4 117.3(3)
C3 O2 C5 115.7(3)
O1 C4 H4A 109.5
O1 C4 H4B 109.5
H4A C4 H4B 109.5
O1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O2 C5 H5A 109.5
O2 C5 H5B 109.5
H5A C5 H5B 109.5
O2 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N3 C6 H6A 109.5
N3 C6 H6B 109.5
H6A C6 H6B 109.5
N3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C1 1.659(4)
C1 N1 1.360(5)
C1 N3 1.398(5)
C2 N1 1.315(5)
C2 O1 1.338(5)
C2 N2 1.350(5)
C3 N2 1.305(5)
C3 O2 1.326(5)
C3 N3 1.362(5)
C4 O1 1.446(5)
C5 O2 1.469(5)
C6 N3 1.474(5)
C4 H4A .9600
C4 H4B .9600
C4 H4C .9600
C5 H5A .9600
C5 H5B .9600
C5 H5C .9600
C6 H6A .9600
C6 H6B .9600
C6 H6C .9600
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
O1 C2 N1 C1 179.0(4)
N2 C2 N1 C1 -2.0(6)
N3 C1 N1 C2 1.6(5)
S C1 N1 C2 -177.8(3)
O2 C3 N2 C2 -178.1(4)
N3 C3 N2 C2 3.2(6)
N1 C2 N2 C3 -.3(6)
O1 C2 N2 C3 178.8(4)
N2 C3 N3 C1 -3.6(6)
O2 C3 N3 C1 177.6(3)
N2 C3 N3 C6 176.7(4)
O2 C3 N3 C6 -2.0(6)
N1 C1 N3 C3 1.0(5)
S C1 N3 C3 -179.6(3)
N1 C1 N3 C6 -179.4(4)
S C1 N3 C6 .0(5)
N1 C2 O1 C4 -2.4(6)
N2 C2 O1 C4 178.5(4)
N2 C3 O2 C5 2.3(6)
N3 C3 O2 C5 -178.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21140529
