#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/43/7204385.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_7204385
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            'C5.5 H Cl4 N5 S4'
_chemical_formula_weight         407.15
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 103.22(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.140(5)
_cell_length_b                   6.7242(15)
_cell_length_c                   10.004(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1384.4(6)
_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 P4'
_diffrn_measurement_method       'ω 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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2459
_diffrn_reflns_theta_max         32.49
_diffrn_reflns_theta_min         1.98
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.445
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_description       needles
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.084
_refine_ls_goodness_of_fit_obs   1.128
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.142
_refine_ls_restrained_S_obs      1.127
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_obs          0.0417
_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)+(0.0735P)²+0.0663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1202
_refine_ls_wR_factor_obs         0.1060
_reflns_number_observed          1942
_reflns_number_total             2410
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b202211g.txt
_cod_data_source_block           6
_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:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+0.0663P] 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^)+(0.0735P)^2^+0.0663P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      C2/m
_cod_original_formula_sum        'C5.50 H N5 S4 Cl4'
_cod_database_code               7204385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
S1 S 0.26296(3) 0.0000 0.68505(7) 0.0390(2) Uani 1 d S .
S2 S 0.30370(4) 0.0000 0.51390(7) 0.0462(2) Uani 1 d S .
N3 N 0.38057(11) 0.0000 0.5959(2) 0.0387(5) Uani 1 d S .
C4 C 0.39175(12) 0.0000 0.7267(3) 0.0326(5) Uani 1 d S .
Cl4 Cl 0.47007(3) 0.0000 0.82130(8) 0.0523(2) Uani 1 d S .
C5 C 0.33879(11) 0.0000 0.7989(2) 0.0281(4) Uani 1 d S .
N6 N 0.34929(10) 0.0000 0.9317(2) 0.0302(4) Uani 1 d S .
N7 N 0.29227(9) 0.0000 0.9761(2) 0.0283(4) Uani 1 d S .
C8 C 0.29739(12) 0.0000 1.1073(2) 0.0290(4) Uani 1 d S .
Cl8 Cl 0.37136(3) 0.0000 1.22567(6) 0.0405(2) Uani 1 d S .
N9 N 0.24550(10) 0.0000 1.1655(2) 0.0301(4) Uani 1 d S .
C10 C 0.18747(11) 0.0000 1.0857(2) 0.0270(4) Uani 1 d S .
S11 S 0.16612(3) 0.0000 0.90780(6) 0.0314(2) Uani 1 d S .
S12 S 0.06705(3) 0.0000 0.90204(8) 0.0451(2) Uani 1 d S .
N13 N 0.07253(11) 0.0000 1.0675(3) 0.0396(5) Uani 1 d S .
C14 C 0.13019(12) 0.0000 1.1428(3) 0.0313(5) Uani 1 d S .
Cl14 Cl 0.14005(4) 0.0000 1.31816(7) 0.0437(2) Uani 1 d S .
C20 C 0.0041(13) 0.1258(26) 0.5195(35) 0.093(7) Uani 0.25 d PD -1
H20A H 0.0239(13) 0.2178(26) 0.4666(35) 0.112 Uiso 0.25 calc PR -1
H20B H -0.0034(13) 0.1961(26) 0.5992(35) 0.112 Uiso 0.25 calc PR -1
Cl21 Cl 0.0564(6) -0.0736(31) 0.5729(8) 0.128(6) Uani 0.25 d PD -1
Cl22 Cl -0.0705(5) 0.0418(19) 0.4187(5) 0.072(3) Uani 0.25 d PD -1
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'
Cl Cl 0.1484 0.1585 '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 92.62(8) . . ?
C5 S1 N7 51.39(9) . . ?
S2 S1 N7 144.01(5) . . ?
C5 S1 S11 100.14(8) . . ?
S2 S1 S11 167.24(4) . . ?
N7 S1 S11 48.75(5) . . ?
N3 S2 S1 97.87(9) . . ?
N3 S2 Cl8 82.40(8) . 1_554 ?
S1 S2 Cl8 179.74(4) . 1_554 ?
N3 S2 Cl14 176.73(9) . 1_554 ?
S1 S2 Cl14 85.40(4) . 1_554 ?
Cl8 S2 Cl14 94.33(3) 1_554 1_554 ?
C4 N3 S2 116.2(2) . . ?
N3 C4 C5 121.5(2) . . ?
N3 C4 Cl4 119.8(2) . . ?
C5 C4 Cl4 118.7(2) . . ?
N6 C5 C4 122.3(2) . . ?
N6 C5 S1 125.9(2) . . ?
C4 C5 S1 111.8(2) . . ?
C5 N6 N7 111.9(2) . . ?
C8 N7 N6 116.8(2) . . ?
C8 N7 S11 96.3(2) . . ?
N6 N7 S11 146.8(2) . . ?
C8 N7 S1 172.4(2) . . ?
N6 N7 S1 70.75(12) . . ?
S11 N7 S1 76.08(6) . . ?
N7 C8 N9 123.3(2) . . ?
N7 C8 Cl8 123.2(2) . . ?
N9 C8 Cl8 113.5(2) . . ?
C10 N9 C8 118.6(2) . . ?
N9 C10 C14 120.8(2) . . ?
N9 C10 S11 128.1(2) . . ?
C14 C10 S11 111.1(2) . . ?
C10 S11 S12 93.01(8) . . ?
C10 S11 N7 73.68(9) . . ?
S12 S11 N7 166.70(6) . . ?
C10 S11 S1 128.85(8) . . ?
S12 S11 S1 138.14(4) . . ?
N7 S11 S1 55.16(5) . . ?
C10 S11 Cl22 159.1(2) . 5_556 ?
S12 S11 Cl22 66.71(14) . 5_556 ?
N7 S11 Cl22 126.53(14) . 5_556 ?
S1 S11 Cl22 71.58(14) . 5_556 ?
N13 S12 S11 97.71(9) . . ?
N13 S12 N13 75.13(11) . 5_557 ?
S11 S12 N13 172.84(6) . 5_557 ?
N13 S12 Cl22 172.8(2) . 5_556 ?
S11 S12 Cl22 77.1(2) . 5_556 ?
N13 S12 Cl22 110.0(2) 5_557 5_556 ?
N13 S12 Cl21 171.3(4) . . ?
S11 S12 Cl21 82.3(2) . . ?
N13 S12 Cl21 104.8(2) 5_557 . ?
Cl22 S12 Cl21 6.3(5) 5_556 . ?
C14 N13 S12 115.8(2) . . ?
N13 C14 C10 122.4(2) . . ?
N13 C14 Cl14 118.6(2) . . ?
C10 C14 Cl14 119.0(2) . . ?
Cl21 C20 Cl22 110.6(14) . . ?
C20 Cl21 S12 94.8(13) . . ?
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 1.741(2) . ?
S1 S2 2.0852(11) . ?
S1 N7 2.835(2) . ?
S1 S11 3.3531(12) . ?
S2 N3 1.644(3) . ?
S2 Cl8 3.4995(13) 1_554 ?
S2 Cl14 3.5645(15) 1_554 ?
N3 C4 1.276(3) . ?
C4 C5 1.464(3) . ?
C4 Cl4 1.709(3) . ?
C5 N6 1.296(3) . ?
N6 N7 1.377(3) . ?
N7 C8 1.291(3) . ?
N7 S11 2.597(2) . ?
C8 N9 1.354(3) . ?
C8 Cl8 1.732(3) . ?
N9 C10 1.302(3) . ?
C10 C14 1.452(3) . ?
C10 S11 1.733(2) . ?
S11 S12 2.0818(10) . ?
S11 Cl22 3.437(7) 5_556 ?
S12 N13 1.633(3) . ?
S12 N13 3.035(2) 5_557 ?
S12 Cl22 3.239(4) 5_556 ?
S12 Cl21 3.286(8) . ?
N13 C14 1.278(4) . ?
C14 Cl14 1.718(3) . ?
C20 Cl21 1.74(2) . ?
C20 Cl22 1.76(2) . ?
