#------------------------------------------------------------------------------
#$Date: 2015-09-26 04:31:02 +0200 (Sat 26 de Sep de 2015) $
#$Revision: 158377 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241126.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_2241126
loop_
_publ_author_name
'Yeo, Chien Ing'
'Tan, Yee Seng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structures of
 5-amino-N-phenyl-3H-1,2,4-dithiazol-3-iminium chloride and
 5-amino-N-(4-chlorophenyl)-3H-1,2,4-dithiazol-3-iminium
 chloride monohydrate
;
_journal_coeditor_code           HB7500
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1159
_journal_page_last               1164
_journal_paper_doi               10.1107/S2056989015016655
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C8 H8 N3 S2 +, Cl -'
_chemical_formula_moiety         'C8 H8 N3 S2 +, Cl -'
_chemical_formula_sum            'C8 H8 Cl N3 S2'
_chemical_formula_weight         245.74
_chemical_name_systematic
;
5-Amino-N-phenyl-3H-1,2,4-dithiazol-3-iminium chloride
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5702(4)
_cell_length_b                   10.8637(7)
_cell_length_c                   14.4964(10)
_cell_measurement_reflns_used    2635
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.34
_cell_volume                     1034.70(12)
_computing_cell_refinement
;
APEX2 (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway,
2001) and
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and 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  0.0443
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9875
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.343
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.8979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.212
_refine_ls_abs_structure_details
;
Flack x determined using 842 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0276
_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)+(0.0242P)²+0.0389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0581
_reflns_number_gt                2185
_reflns_number_total             2378
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7500sup1.cif
_cod_data_source_block           I
_cod_database_code               2241126
_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   0.898
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_occupancy
S S1 1.07530(11) 0.36767(6) 0.26929(5) 0.01784(16) Uani d 1
S S2 0.85079(11) 0.48700(7) 0.22480(5) 0.01919(17) Uani d 1
N N1 1.0681(4) 0.2920(2) 0.44270(15) 0.0173(5) Uani d 1
H H1N 1.027(4) 0.297(3) 0.4995(11) 0.021 Uiso d 1
H H2N 1.182(3) 0.255(3) 0.4263(19) 0.021 Uiso d 1
N N2 0.8085(3) 0.4255(2) 0.40293(14) 0.0140(5) Uani d 1
N N3 0.5664(4) 0.5602(2) 0.33970(16) 0.0175(5) Uani d 1
H H3N 0.540(4) 0.605(2) 0.2910(14) 0.021 Uiso d 1
C C1 0.9739(4) 0.3609(2) 0.38220(17) 0.0144(6) Uani d 1
C C2 0.7320(4) 0.4904(3) 0.33453(18) 0.0156(6) Uani d 1
C C3 0.4216(4) 0.5731(2) 0.41161(18) 0.0153(6) Uani d 1
C C4 0.4307(4) 0.5100(2) 0.49499(18) 0.0162(6) Uani d 1
H H4 0.5415 0.4567 0.5083 0.019 Uiso calc 1
C C5 0.2751(4) 0.5264(3) 0.55831(19) 0.0173(6) Uani d 1
H H5 0.2780 0.4817 0.6146 0.021 Uiso calc 1
C C6 0.1161(4) 0.6061(3) 0.54155(19) 0.0194(6) Uani d 1
H H6 0.0121 0.6173 0.5863 0.023 Uiso calc 1
C C7 0.1093(5) 0.6702(3) 0.45801(19) 0.0202(7) Uani d 1
H H7 0.0006 0.7255 0.4458 0.024 Uiso calc 1
C C8 0.2609(4) 0.6529(3) 0.39322(19) 0.0180(6) Uani d 1
H H8 0.2554 0.6956 0.3361 0.022 Uiso calc 1
Cl Cl1 0.53467(10) 0.70982(6) 0.15949(4) 0.01812(16) Uani d 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
C1 S1 S2 92.63(9)
C2 S2 S1 92.72(10)
C1 N1 H1N 117.0(19)
C1 N1 H2N 119(2)
H1N N1 H2N 123(3)
C2 N2 C1 115.1(2)
C2 N3 C3 130.4(2)
C2 N3 H3N 116(2)
C3 N3 H3N 114(2)
N1 C1 N2 122.5(2)
N1 C1 S1 117.8(2)
N2 C1 S1 119.7(2)
N2 C2 N3 125.2(2)
N2 C2 S2 119.8(2)
N3 C2 S2 115.1(2)
C4 C3 C8 120.4(3)
C4 C3 N3 124.1(2)
C8 C3 N3 115.5(2)
C5 C4 C3 118.7(3)
C5 C4 H4 120.6
C3 C4 H4 120.6
C6 C5 C4 121.6(3)
C6 C5 H5 119.2
C4 C5 H5 119.2
C5 C6 C7 119.3(3)
C5 C6 H6 120.3
C7 C6 H6 120.3
C8 C7 C6 119.9(3)
C8 C7 H7 120.1
C6 C7 H7 120.1
C7 C8 C3 120.1(3)
C7 C8 H8 120.0
C3 C8 H8 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.769(3)
S1 S2 2.0669(10)
S2 C2 1.772(3)
N1 C1 1.309(3)
N1 H1N 0.869(13)
N1 H2N 0.881(13)
N2 C2 1.317(3)
N2 C1 1.328(3)
N3 C2 1.328(3)
N3 C3 1.418(3)
N3 H3N 0.875(12)
C3 C4 1.391(4)
C3 C8 1.392(4)
C4 C5 1.386(4)
C4 H4 0.9500
C5 C6 1.378(4)
C5 H5 0.9500
C6 C7 1.398(4)
C6 H6 0.9500
C7 C8 1.382(4)
C7 H7 0.9500
C8 H8 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N Cl1 2_665 0.868(17) 2.356(16) 3.215(2) 170(3)
N1 H2N Cl1 3_745 0.88(2) 2.29(2) 3.131(3) 159(3)
N3 H3N Cl1 . 0.88(2) 2.22(2) 3.084(2) 169(2)
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
C2 N2 C1 N1 179.8(3)
C2 N2 C1 S1 0.4(3)
S2 S1 C1 N1 -179.9(2)
S2 S1 C1 N2 -0.5(2)
C1 N2 C2 N3 179.2(2)
C1 N2 C2 S2 -0.1(3)
C3 N3 C2 N2 -7.6(5)
C3 N3 C2 S2 171.6(2)
S1 S2 C2 N2 -0.2(2)
S1 S2 C2 N3 -179.5(2)
C2 N3 C3 C4 0.2(4)
C2 N3 C3 C8 -178.3(3)
C8 C3 C4 C5 1.2(4)
N3 C3 C4 C5 -177.2(2)
C3 C4 C5 C6 -1.9(4)
C4 C5 C6 C7 1.2(4)
C5 C6 C7 C8 0.2(4)
C6 C7 C8 C3 -0.9(4)
C4 C3 C8 C7 0.2(4)
N3 C3 C8 C7 178.7(2)

_cod_database_fobs_code 2241126
