#------------------------------------------------------------------------------
#$Date: 2015-06-04 06:07:58 +0300 (Thu, 04 Jun 2015) $
#$Revision: 137793 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/30/4513077.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_4513077
loop_
_publ_author_name
'Yutronkie, Nathan J.'
'Leitch, Alicea A.'
'Korobkov, Ilia'
'Brusso, Jaclyn L.'
_publ_section_title
;
 1,2,4,6-Thiatriazinyl Radicals and Dimers: Structural and Electronic
 Tuning through Heteroaromatic Substituent Modification
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2524
_journal_paper_doi               10.1021/acs.cgd.5b00296
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C10 H7 N3 O S3'
_chemical_formula_weight         281.37
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.627(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3997(12)
_cell_length_b                   4.2844(5)
_cell_length_c                   14.2053(16)
_cell_measurement_reflns_used    3032
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.57
_cell_volume                     571.85(12)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_laue_measured_fraction_full 0.993
_diffrn_reflns_laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5493
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_min         1.434
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     394
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0440P)²+0.0318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.772
_reflns_friedel_fraction_full    0.997
_reflns_friedel_fraction_max     0.993
_reflns_number_gt                2116
_reflns_number_total             2617
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b00296_si_006.cif
_cod_data_source_block           jb023
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_database_code               4513077
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.37252(11) 0.2696(2) 0.89562(6) 0.0349(3) Uani 1 1 d . U . . .
N1 N 0.5255(3) 0.6313(8) 0.7452(2) 0.0315(7) Uani 1 1 d . U . . .
N2 N 0.5502(3) 0.3148(9) 0.8791(2) 0.0364(8) Uani 1 1 d . U . . .
H2A H 0.6104 0.1997 0.9126 0.044 Uiso 1 1 calc R U . . .
N3 N 0.3139(3) 0.3506(8) 0.7882(2) 0.0351(8) Uani 1 1 d . U . . .
O1 O 0.3298(3) 0.5274(7) 0.95669(17) 0.0383(7) Uani 1 1 d . U . . .
C1 C 0.6017(4) 0.5190(9) 0.8172(2) 0.0294(8) Uani 1 1 d . U . . .
C2 C 0.3897(4) 0.5225(9) 0.7326(2) 0.0287(8) Uani 1 1 d . U . . .
C3 C 0.7499(4) 0.6134(10) 0.8264(3) 0.0337(9) Uani 1 1 d . U . . .
C4 C 0.8491(5) 0.5422(12) 0.8984(3) 0.0426(11) Uani 1 1 d D U . . .
H4A H 0.8279 0.4233 0.9527 0.051 Uiso 1 1 calc R U . . .
C5 C 0.9821(5) 0.6658(13) 0.8811(3) 0.0548(13) Uani 1 1 d D U . . .
H5A H 1.0628 0.6365 0.9219 0.066 Uiso 1 1 calc R U . . .
C6 C 0.9853(4) 0.8306(14) 0.8011(3) 0.0559(13) Uani 1 1 d D U . . .
H6A H 1.0679 0.9337 0.7798 0.067 Uiso 1 1 calc R U . . .
S2 S 0.82498(11) 0.8355(3) 0.74146(7) 0.0484(4) Uani 1 1 d D U . . .
C7 C 0.3240(4) 0.6068(9) 0.6412(2) 0.0314(9) Uani 1 1 d . U . . .
C8 C 0.3816(19) 0.768(5) 0.5682(12) 0.065(5) Uani 0.61 1 d D U P A 1
H8A H 0.4752 0.8514 0.5728 0.078 Uiso 0.61 1 calc R U P A 1
C9 C 0.2977(18) 0.805(7) 0.4878(13) 0.045(3) Uani 0.61 1 d D U P A 1
H9A H 0.3241 0.9170 0.4332 0.054 Uiso 0.61 1 calc R U P A 1
C10 C 0.1711(18) 0.657(5) 0.4986(9) 0.040(3) Uani 0.61 1 d D U P A 1
H10A H 0.0979 0.6503 0.4511 0.047 Uiso 0.61 1 calc R U P A 1
S3 S 0.1570(4) 0.4799(14) 0.6091(3) 0.0400(9) Uani 0.61 1 d D U P A 1
C8' C 0.186(3) 0.509(9) 0.6056(19) 0.038(5) Uani 0.39 1 d D U P A 2
H8B H 0.1210 0.3879 0.6401 0.045 Uiso 0.39 1 calc R U P A 2
C9' C 0.162(3) 0.613(8) 0.5163(17) 0.051(5) Uani 0.39 1 d D U P A 2
H9B H 0.0785 0.5663 0.4792 0.062 Uiso 0.39 1 calc R U P A 2
C10' C 0.271(3) 0.792(11) 0.4869(19) 0.044(6) Uani 0.39 1 d D U P A 2
H10B H 0.2712 0.8890 0.4267 0.053 Uiso 0.39 1 calc R U P A 2
S3' S 0.4092(6) 0.8274(17) 0.5690(4) 0.0443(12) Uani 0.39 1 d D U P A 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 N3 107.43(17)
O1 S1 N2 106.33(17)
N3 S1 N2 98.75(16)
C1 N1 C2 117.5(3)
C1 N2 S1 122.6(3)
C2 N3 S1 120.4(3)
N1 C1 N2 123.1(4)
N1 C1 C3 117.8(4)
N2 C1 C3 119.1(3)
N3 C2 N1 129.6(3)
N3 C2 C7 116.8(3)
N1 C2 C7 113.6(3)
C4 C3 C1 128.6(4)
C4 C3 S2 111.0(3)
C1 C3 S2 120.4(3)
C5 C4 C3 112.0(4)
C6 C5 C4 113.2(4)
C5 C6 S2 112.7(4)
C3 S2 C6 91.1(2)
C8 C7 C2 129.0(8)
C8' C7 C2 126.3(10)
C8' C7 S3' 113.7(10)
C2 C7 S3' 120.0(4)
C8 C7 S3 109.7(7)
C2 C7 S3 121.2(3)
C9 C8 C7 117.1(15)
C10 C9 C8 109.5(16)
C9 C10 S3 113.1(11)
C7 S3 C10 90.5(6)
C9' C8' C7 111.1(19)
C10' C9' C8' 111(2)
C9' C10' S3' 113.8(19)
C7 S3' C10' 90.0(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.468(3)
S1 N3 1.645(3)
S1 N2 1.704(3)
N1 C1 1.323(4)
N1 C2 1.365(5)
N2 C1 1.341(5)
N3 C2 1.306(5)
C1 C3 1.452(5)
C2 C7 1.467(5)
C3 C4 1.397(5)
C3 S2 1.706(4)
C4 C5 1.386(6)
C5 C6 1.339(7)
C6 S2 1.708(4)
C7 C8 1.371(19)
C7 C8' 1.44(2)
C7 S3' 1.623(8)
C7 S3 1.712(5)
C8 C9 1.379(17)
C9 C10 1.361(12)
C10 S3 1.751(11)
C8' C9' 1.36(2)
C9' C10' 1.358(17)
C10' S3' 1.728(18)
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 S1 N2 C1 -79.7(3)
N3 S1 N2 C1 31.4(3)
O1 S1 N3 C2 86.1(3)
N2 S1 N3 C2 -24.1(3)
C2 N1 C1 N2 -2.5(5)
C2 N1 C1 C3 174.9(3)
S1 N2 C1 N1 -21.1(5)
S1 N2 C1 C3 161.5(3)
S1 N3 C2 N1 7.6(6)
S1 N3 C2 C7 -174.6(3)
C1 N1 C2 N3 10.1(6)
C1 N1 C2 C7 -167.7(3)
N1 C1 C3 C4 176.0(4)
N2 C1 C3 C4 -6.6(6)
N1 C1 C3 S2 -5.3(5)
N2 C1 C3 S2 172.2(3)
C1 C3 C4 C5 177.9(4)
S2 C3 C4 C5 -1.0(5)
C3 C4 C5 C6 1.4(6)
C4 C5 C6 S2 -1.3(6)
C4 C3 S2 C6 0.2(4)
C1 C3 S2 C6 -178.7(3)
C5 C6 S2 C3 0.6(4)
N3 C2 C7 C8 -176.1(13)
N1 C2 C7 C8 2.0(13)
N3 C2 C7 C8' -2(2)
N1 C2 C7 C8' 176(2)
N3 C2 C7 S3' 178.4(4)
N1 C2 C7 S3' -3.5(6)
N3 C2 C7 S3 -0.9(6)
N1 C2 C7 S3 177.2(4)
C8' C7 C8 C9 3(3)
C2 C7 C8 C9 177.4(18)
S3' C7 C8 C9 -154(8)
S3 C7 C8 C9 2(3)
C7 C8 C9 C10 -2(3)
C8 C9 C10 S3 1(3)
C8 C7 S3 C10 -0.9(13)
C8' C7 S3 C10 -10(20)
C2 C7 S3 C10 -177.0(8)
S3' C7 S3 C10 3.7(9)
C9 C10 S3 C7 -0.1(17)
C8 C7 C8' C9' -1(4)
C2 C7 C8' C9' -176(2)
S3' C7 C8' C9' 3(4)
S3 C7 C8' C9' 170(23)
C7 C8' C9' C10' -3(5)
C8' C9' C10' S3' 2(5)
C8 C7 S3' C10' 23(6)
C8' C7 S3' C10' -2(3)
C2 C7 S3' C10' 177.5(17)
S3 C7 S3' C10' -3.2(18)
C9' C10' S3' C7 0(3)
