#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/43/7204386.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_7204386
loop_
_publ_author_name
'Rees, Charles W.'
'Sivadasan, Sivaprasad'
'White, Andrew J. P.'
'Williams, David J.'
_publ_section_title
;
 Conversion of tetrazoles into hydrazonoyl chlorides. Novel
 donor--dithiazolium interactions
;
_journal_issue                   13
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1535
_journal_paper_doi               10.1039/b202211g
_journal_year                    2002
_chemical_formula_sum            'C8 H6 Cl N3 O2 S4'
_chemical_formula_weight         339.85
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                112.17(2)
_cell_angle_beta                 97.07(2)
_cell_angle_gamma                100.08(2)
_cell_formula_units_Z            2
_cell_length_a                   8.314(2)
_cell_length_b                   9.068(3)
_cell_length_c                   9.915(3)
_cell_measurement_temperature    293(2)
_cell_volume                     666.7(4)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P3'
_diffrn_measurement_method       'ω scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1774
_diffrn_reflns_theta_max         56.70
_diffrn_reflns_theta_min         4.92
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    8.390
_exptl_absorpt_correction_T_max  0.3120
_exptl_absorpt_correction_T_min  0.1507
_exptl_absorpt_correction_type   Ellipsoidal
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_description       blocks
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0064(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.039
_refine_ls_goodness_of_fit_obs   1.060
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_restrained_S_obs      1.060
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_obs          0.0382
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0628P)²+0.6804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1153
_refine_ls_wR_factor_obs         0.1017
_reflns_number_observed          1609
_reflns_number_total             1774
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b202211g.txt
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+0.6804P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+0.6804P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        666.8(3)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C8 H6 N3 O2 S4 Cl'
_cod_database_code               7204386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
S1 S 0.36592(10) 0.35351(10) 0.56174(9) 0.0371(3) Uani 1 d . .
S2 S 0.37587(11) 0.11765(10) 0.43374(10) 0.0419(3) Uani 1 d . .
N3 N 0.2710(4) 0.1026(3) 0.2784(3) 0.0425(7) Uani 1 d . .
C4 C 0.2165(4) 0.2283(4) 0.2811(4) 0.0369(8) Uani 1 d . .
Cl4 Cl 0.10838(15) 0.21499(12) 0.11750(10) 0.0657(4) Uani 1 d . .
C5 C 0.2485(4) 0.3731(4) 0.4178(3) 0.0317(7) Uani 1 d . .
C6 C 0.1985(4) 0.5187(4) 0.4427(3) 0.0323(7) Uani 1 d . .
N7 N 0.1031(3) 0.5490(3) 0.3359(3) 0.0377(7) Uani 1 d . .
C8 C 0.0817(4) 0.6955(4) 0.3933(4) 0.0387(8) Uani 1 d . .
S9 S 0.16799(12) 0.81741(11) 0.57967(10) 0.0478(3) Uani 1 d . .
C10 C 0.2496(4) 0.6510(4) 0.5874(4) 0.0378(8) Uani 1 d . .
O10 O 0.3368(3) 0.6540(3) 0.6971(3) 0.0515(7) Uani 1 d . .
C11 C -0.0102(5) 0.7604(5) 0.3058(4) 0.0473(9) Uani 1 d . .
N11 N -0.0836(5) 0.8134(5) 0.2387(4) 0.0666(10) Uani 1 d . .
S20 S 0.55507(14) 0.30713(13) 0.86775(10) 0.0561(4) Uani 1 d . .
O20 O 0.5625(4) 0.2112(3) 0.7095(3) 0.0557(7) Uani 1 d . .
C21 C 0.7618(6) 0.3655(7) 0.9705(5) 0.083(2) Uani 1 d . .
H21A H 0.8275(6) 0.4477(7) 0.9474(5) 0.124 Uiso 1 calc R .
H21B H 0.8088(6) 0.2715(7) 0.9448(5) 0.124 Uiso 1 calc R .
H21C H 0.7616(6) 0.4092(7) 1.0750(5) 0.124 Uiso 1 calc R .
C22 C 0.4742(6) 0.1611(7) 0.9353(5) 0.0801(15) Uani 1 d . .
H22A H 0.3580(6) 0.1140(7) 0.8901(5) 0.120 Uiso 1 calc R .
H22B H 0.4868(6) 0.2138(7) 1.0414(5) 0.120 Uiso 1 calc R .
H22C H 0.5340(6) 0.0761(7) 0.9113(5) 0.120 Uiso 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 0.0181 0.0091 '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 0.0311 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'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 S2 93.61(12) . . ?
C5 S1 O10 80.04(13) . . ?
S2 S1 O10 173.62(7) . . ?
C5 S1 O20 158.36(12) . . ?
S2 S1 O20 64.97(6) . . ?
O10 S1 O20 121.32(8) . . ?
N3 S2 S1 97.27(11) . . ?
N3 S2 O20 168.01(13) . . ?
S1 S2 O20 71.59(7) . . ?
N3 S2 O20 91.88(12) . 2_656 ?
S1 S2 O20 170.35(7) . 2_656 ?
O20 S2 O20 99.03(7) . 2_656 ?
C4 N3 S2 116.8(2) . . ?
N3 C4 C5 120.4(3) . . ?
N3 C4 Cl4 117.2(3) . . ?
C5 C4 Cl4 122.3(3) . . ?
C6 C5 C4 128.6(3) . . ?
C6 C5 S1 119.5(2) . . ?
C4 C5 S1 111.8(2) . . ?
N7 C6 C5 124.9(3) . . ?
N7 C6 C10 115.5(3) . . ?
C5 C6 C10 119.6(3) . . ?
C8 N7 C6 109.7(3) . . ?
N7 C8 C11 121.3(3) . . ?
N7 C8 S9 119.1(3) . . ?
C11 C8 S9 119.5(3) . . ?
C8 S9 C10 87.7(2) . . ?
O10 C10 C6 127.1(3) . . ?
O10 C10 S9 124.9(3) . . ?
C6 C10 S9 107.9(2) . . ?
C10 O10 S1 93.7(2) . . ?
N11 C11 C8 178.8(4) . . ?
O20 S20 C21 105.9(2) . . ?
O20 S20 C22 106.0(2) . . ?
C21 S20 C22 97.3(2) . . ?
S20 O20 S2 138.3(2) . . ?
S20 O20 S1 100.75(13) . . ?
S2 O20 S1 43.44(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.712(3) . ?
S1 S2 2.0570(14) . ?
S1 O10 2.614(3) . ?
S1 O20 2.839(3) . ?
S2 N3 1.619(3) . ?
S2 O20 2.711(3) . ?
S2 O20 2.948(3) 2_656 ?
N3 C4 1.290(5) . ?
C4 C5 1.442(5) . ?
C4 Cl4 1.706(3) . ?
C5 C6 1.395(5) . ?
C6 N7 1.384(4) . ?
C6 C10 1.432(5) . ?
N7 C8 1.287(4) . ?
C8 C11 1.436(5) . ?
C8 S9 1.733(4) . ?
S9 C10 1.782(3) . ?
C10 O10 1.220(4) . ?
C11 N11 1.136(5) . ?
S20 O20 1.495(3) . ?
S20 C21 1.765(5) . ?
S20 C22 1.767(5) . ?
