#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/94/2019436.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_2019436
loop_
_publ_author_name
'Jones, Ray'
_publ_section_title
;
 Three trithiadiazepines and a trithiatriazepine
;
_journal_coeditor_code           QS3029
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              60
_journal_page_last               66
_journal_paper_doi               10.1107/S2053229613033287
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C2 N4 O4 S3'
_chemical_formula_moiety         'C2 N4 O4 S3'
_chemical_formula_sum            'C2 N4 O4 S3'
_chemical_formula_weight         240.24
_chemical_melting_point          336
_chemical_name_systematic
;
6,7-Dinitro-1,3,5,2,4-trithiadiazepine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.36(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.182(2)
_cell_length_b                   8.436(2)
_cell_length_c                   8.609(2)
_cell_measurement_reflns_used    11
_cell_measurement_temperature    293(2)
_cell_volume                     811.9(3)
_computing_cell_refinement       'Nicolet R3m software'
_computing_data_collection       'Nicolet R3m software'
_computing_data_reduction        'Nicolet R3m software'
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009) and
Mercury (Macrae et al., 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS83 (Sheldrick, 1983)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nicolet R3m'
_diffrn_measurement_method       'Scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            581
_diffrn_reflns_theta_full        56.97
_diffrn_reflns_theta_max         56.97
_diffrn_reflns_theta_min         6.57
_diffrn_standards_decay_%        10
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    8.375
_exptl_absorpt_correction_T_max  0.4700
_exptl_absorpt_correction_T_min  0.3800
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(SHELXS83; Sheldrick, 1983)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.965
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.158
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0250
_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
 [1.00000+0.00000exp(0.00(sinθ/λ)²)]/
   [σ²(Fo²)+0.0000+0.7454*P+(0.0347P)²+1.0000sinθ/λ]
 where P = 0.33333Fo² + 0.66667Fc²
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0658
_reflns_number_gt                511
_reflns_number_total             543
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL (2) 6,7-Dinitro-1,3,5,2,4-trithiadiazepine
CELL 1.54178 11.182 8.436 8.609 90 91.36 90
ZERR 4 0.002 0.002 0.002 0 0.02 0
LATT 2
SYMM 0.5-X,+Y,-Z
SFAC C N O S
UNIT 8 16 16 12
DEFS 0.002 0.2 0.01 0.05 1
L.S. 10
PLAN  20
SIZE 0.1 0.1 0.15
TEMP 20
MORE 3
LIST 4
CONF
HTAB
BOND $H
FMAP
ACTA
WPDB
WGHT    0.034700    0.745400    0.000000    0.000000    1.000000
EXTI    0.002207
FVAR       1.22436
S1    4    0.109380    0.645852    0.369732    11.00000    0.04077    0.05173 =
         0.05469   -0.00568   -0.00888   -0.01081
N2    2    0.149240    0.469823    0.411939    11.00000    0.06220    0.04511 =
         0.07220   -0.00876    0.00058   -0.01522
S3    4   10.250000    0.379593   10.500000    10.50000    0.07654    0.03665 =
         0.08497    0.00000    0.00841    0.00000
C7    1    0.199754    0.787418    0.454066    11.00000    0.02983    0.03835 =
         0.03873    0.00069   -0.00027   -0.00152
N8    2    0.142315    0.941037    0.416308    11.00000    0.02756    0.04700 =
         0.05504    0.00732   -0.00294    0.00190
O9    3    0.106646    0.958330    0.281630    11.00000    0.06015    0.07914 =
         0.06183    0.01802   -0.01394    0.01918
O10   3    0.129046    1.036535    0.519644    11.00000    0.04405    0.04372 =
         0.07731   -0.00717   -0.00066    0.00717
HKLF 4 1 0 0 1 0 -1 0 1 0 0
REM  (2) 6,7-Dinitro-1,3,5,2,4-trithiadiazepine$
REM R1 =  0.0250 for    511 Fo > 4sig(Fo)  and  0.0265 for all    543 data
REM     61 parameters refined using      0 restraints
END
WGHT      0.0346      0.7723
REM Highest difference peak  0.229,  deepest hole -0.158,  1-sigma level  0.043
Q1    1   0.1610  0.7196  0.4250  11.00000  0.05    0.23
Q2    1   0.1533  0.5532  0.4132  11.00000  0.05    0.21
Q3    1   0.1816  0.4381  0.4745  11.00000  0.05    0.18
Q4    1   0.2300  0.7789  0.5318  11.00000  0.05    0.15
Q5    1   0.1116  0.4388  0.3769  11.00000  0.05    0.14
Q6    1   0.1888  0.8450  0.4462  11.00000  0.05    0.13
Q7    1   0.0390  0.8743  0.3025  11.00000  0.05    0.13
Q8    1   0.0270  0.7295  0.3245  11.00000  0.05    0.12
Q9    1   0.0285  1.0176  0.2817  11.00000  0.05    0.12
Q10   1   0.1340  0.6512  0.2434  11.00000  0.05    0.12
Q11   1   0.2500  1.1137  0.5000  10.50000  0.05    0.11
Q12   1   0.2500  0.2841  0.5000  10.50000  0.05    0.11
Q13   1   0.0504  1.1489  0.3543  11.00000  0.05    0.10
Q14   1   0.1570  1.0695  0.5774  11.00000  0.05    0.10
Q15   1   0.0740  1.1509  0.2304  11.00000  0.05    0.09
Q16   1   0.1522  1.0665  0.4366  11.00000  0.05    0.09
Q17   1   0.1994  1.0275  0.5690  11.00000  0.05    0.08
Q18   1   0.0084  0.9667  0.1773  11.00000  0.05    0.08
Q19   1   0.2243  0.3679  0.6029  11.00000  0.05    0.08
Q20   1   0.0188  0.8122  0.2260  11.00000  0.05    0.08
;
_cod_data_source_file            qs3029sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               2019436
_cod_database_fobs_code          2019436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_symmetry_multiplicity
S S1 0.10938(6) 0.64585(8) 0.36973(8) 0.0492(3) Uani d . 1 1
N N2 0.1492(2) 0.4698(3) 0.4119(3) 0.0599(7) Uani d . 1 1
S S3 0.2500 0.37959(11) 0.5000 0.0660(4) Uani d S 1 2
C C7 0.1998(2) 0.7874(3) 0.4541(2) 0.0357(6) Uani d . 1 1
N N8 0.14231(16) 0.9410(2) 0.4163(2) 0.0433(5) Uani d . 1 1
O O9 0.10665(18) 0.9583(2) 0.2816(2) 0.0673(6) Uani d . 1 1
O O10 0.12905(16) 1.0365(2) 0.5196(2) 0.0551(5) Uani d . 1 1
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
S1 0.0408(4) 0.0517(5) 0.0547(5) -0.0108(3) -0.0089(3) -0.0057(3)
N2 0.0622(15) 0.0451(13) 0.0722(16) -0.0152(11) 0.0006(12) -0.0088(11)
S3 0.0765(8) 0.0367(6) 0.0850(8) 0.000 0.0084(6) 0.000
C7 0.0298(11) 0.0384(13) 0.0387(12) -0.0015(10) -0.0003(9) 0.0007(10)
N8 0.0276(11) 0.0470(12) 0.0550(13) 0.0019(9) -0.0029(9) 0.0073(11)
O9 0.0602(13) 0.0791(15) 0.0618(13) 0.0192(10) -0.0139(9) 0.0180(10)
O10 0.0441(11) 0.0437(11) 0.0773(13) 0.0072(8) -0.0007(9) -0.0072(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N2 S1 C7 . 113.24(12)
S3 N2 S1 . 140.36(16)
N2 S3 N2 2_556 120.91(17)
C7 C7 N8 2_556 118.47(11)
C7 C7 S1 2_556 135.85(8)
N8 C7 S1 . 105.59(15)
O10 N8 O9 . 124.9(2)
O10 N8 C7 . 118.76(19)
O9 N8 C7 . 116.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 N2 . 1.590(2)
S1 C7 . 1.715(2)
N2 S3 . 1.544(3)
S3 N2 2_556 1.544(3)
C7 C7 2_556 1.359(4)
C7 N8 . 1.479(3)
N8 O10 . 1.212(3)
N8 O9 . 1.226(3)
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_4
_geom_torsion
C7 S1 N2 S3 . . -4.5(3)
S1 N2 S3 N2 . 2_556 3.01(19)
N2 S1 C7 C7 . 2_556 2.2(4)
N2 S1 C7 N8 . . -174.10(15)
C7 C7 N8 O10 2_556 . -45.2(3)
S1 C7 N8 O10 . . 131.85(18)
C7 C7 N8 O9 2_556 . 138.0(3)
S1 C7 N8 O9 . . -44.9(2)
