#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239883.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_2239883
loop_
_publ_author_name
'Chandrasekaran, Thangayyah'
'Suresh, Mani'
'Josephine Novina, John'
'Syed Ali Padusha, Mohamed Khan'
'Vasuki, Gopalsamy'
'Kasthuri, Balasubramani'
_publ_section_title
;
 Crystal structure of
 3-({[(thiophen-2-yl)methylidene]hydrazinyl}carbonyl)pyridinium chloride
 dihydrate
;
_journal_coeditor_code           WM5042
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o976
_journal_page_last               o977
_journal_paper_doi               10.1107/S1600536814017565
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H10 N3 O S +, Cl -, 2H2 O'
_chemical_formula_moiety         'C11 H10 N3 O S +, Cl -, 2(H2 O)'
_chemical_formula_sum            'C11 H14 Cl N3 O3 S'
_chemical_formula_weight         303.76
_chemical_name_systematic
;
3-({[(Thiophen-2-yl)methylidene]hydrazinyl}carbonyl)pyridinium chloride
dihydrate
;
_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-97
_cell_angle_alpha                67.361(4)
_cell_angle_beta                 78.210(4)
_cell_angle_gamma                77.119(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8781(7)
_cell_length_b                   8.6928(7)
_cell_length_c                   11.0999(10)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.019
_cell_measurement_theta_min      2.572
_cell_volume                     677.97(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
'PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5444
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  0.8786
_exptl_absorpt_correction_T_min  0.8604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.403
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3222
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0760P)²+0.1235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                2761
_reflns_number_total             3222
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wm5042sup1.cif
_cod_data_source_block           I
_cod_database_code               2239883
_cod_database_fobs_code          2239883
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.17836(6) 0.47295(5) 0.80609(4) 0.04223(14) Uani d . 1 1
Cl Cl 0.17151(7) 0.25503(5) 1.42848(4) 0.05065(16) Uani d . 1 1
O O1 0.38027(16) 0.80909(14) 1.00852(10) 0.0399(3) Uani d . 1 1
O O1W 0.3488(2) 0.82526(19) 0.75281(13) 0.0514(3) Uani d D 1 1
N N2 0.31200(17) 0.55367(15) 1.14192(12) 0.0315(3) Uani d . 1 1
N N3 0.27791(16) 0.52406(15) 1.03627(12) 0.0306(3) Uani d . 1 1
O O2W 0.0187(2) 0.9549(2) 0.67510(14) 0.0640(4) Uani d D 1 1
N N1 0.47813(17) 0.91856(17) 1.31029(13) 0.0367(3) Uani d . 1 1
H H1N1 0.5298 1.0037 1.2922 0.044 Uiso calc R 1 1
C C9 0.1401(2) 0.18261(19) 0.98202(16) 0.0367(3) Uani d . 1 1
H H9 0.1335 0.0925 1.0618 0.044 Uiso calc R 1 1
C C4 0.37426(18) 0.74005(17) 1.23659(14) 0.0287(3) Uani d . 1 1
C C6 0.35574(18) 0.70370(17) 1.11885(13) 0.0284(3) Uani d . 1 1
C C5 0.4561(2) 0.87569(19) 1.21193(15) 0.0329(3) Uani d . 1 1
H H5 0.4964 0.9381 1.1257 0.040 Uiso calc R 1 1
C C7 0.23292(19) 0.38064(18) 1.06447(14) 0.0318(3) Uani d . 1 1
H H7 0.2300 0.3041 1.1506 0.038 Uiso calc R 1 1
C C8 0.18671(19) 0.33584(18) 0.96480(14) 0.0306(3) Uani d . 1 1
C C11 0.1187(2) 0.3284(3) 0.76111(18) 0.0471(4) Uani d . 1 1
H H11 0.0986 0.3481 0.6763 0.057 Uiso calc R 1 1
C C10 0.1041(2) 0.1815(2) 0.86327(19) 0.0466(4) Uani d . 1 1
H H10 0.0732 0.0886 0.8558 0.056 Uiso calc R 1 1
C C3 0.3133(3) 0.6516(2) 1.36593(16) 0.0471(4) Uani d . 1 1
H H3 0.2565 0.5600 1.3860 0.056 Uiso calc R 1 1
C C2 0.3378(3) 0.7008(3) 1.46513(17) 0.0610(6) Uani d . 1 1
H H2 0.2962 0.6429 1.5522 0.073 Uiso calc R 1 1
C C1 0.4229(3) 0.8340(2) 1.43523(17) 0.0481(4) Uani d . 1 1
H H1 0.4421 0.8655 1.5019 0.058 Uiso calc R 1 1
H H2N2 0.298(3) 0.482(3) 1.218(2) 0.057(6) Uiso d . 1 1
H H1O1 0.337(4) 0.778(3) 0.8380(17) 0.086(9) Uiso d D 1 1
H H2O2 -0.019(4) 0.898(3) 0.644(3) 0.093(10) Uiso d D 1 1
H H1O2 0.047(3) 1.041(3) 0.610(2) 0.078(8) Uiso d D 1 1
H H2O1 0.243(2) 0.854(3) 0.734(3) 0.079(9) Uiso d D 1 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'
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'
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
C11 S1 C8 92.07(8)
H1O1 O1W H2O1 104(2)
C6 N2 N3 117.65(12)
C6 N2 H2N2 122.4(16)
N3 N2 H2N2 119.8(16)
C7 N3 N2 114.96(12)
H2O2 O2W H1O2 106(2)
C1 N1 C5 122.12(13)
C1 N1 H1N1 118.9
C5 N1 H1N1 118.9
C8 C9 C10 111.34(14)
C8 C9 H9 124.3
C10 C9 H9 124.3
C5 C4 C3 118.07(14)
C5 C4 C6 116.35(12)
C3 C4 C6 125.57(13)
O1 C6 N2 123.36(13)
O1 C6 C4 119.87(12)
N2 C6 C4 116.77(12)
N1 C5 C4 120.82(13)
N1 C5 H5 119.6
C4 C5 H5 119.6
N3 C7 C8 120.85(13)
N3 C7 H7 119.6
C8 C7 H7 119.6
C9 C8 C7 126.41(14)
C9 C8 S1 111.11(11)
C7 C8 S1 122.47(11)
C10 C11 S1 111.95(13)
C10 C11 H11 124.0
S1 C11 H11 124.0
C11 C10 C9 113.50(15)
C11 C10 H10 123.2
C9 C10 H10 123.2
C4 C3 C2 119.31(15)
C4 C3 H3 120.3
C2 C3 H3 120.3
C1 C2 C3 120.10(16)
C1 C2 H2 120.0
C3 C2 H2 120.0
N1 C1 C2 119.56(15)
N1 C1 H1 120.2
C2 C1 H1 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C11 . 1.6999(18)
S1 C8 . 1.7101(15)
Cl Cl 1 0.0000(12)
O1 C6 . 1.2226(17)
O1W H1O1 . 0.868(17)
O1W H2O1 . 0.857(16)
N2 C6 . 1.3389(18)
N2 N3 . 1.3804(17)
N2 H2N2 . 0.83(2)
N3 C7 . 1.2764(18)
O2W H2O2 . 0.837(17)
O2W H1O2 . 0.851(16)
N1 C1 . 1.328(2)
N1 C5 . 1.3344(19)
N1 H1N1 . 0.8600
C9 C8 . 1.393(2)
C9 C10 . 1.408(2)
C9 H9 . 0.9300
C4 C5 . 1.3780(19)
C4 C3 . 1.384(2)
C4 C6 . 1.4985(19)
C5 H5 . 0.9300
C7 C8 . 1.438(2)
C7 H7 . 0.9300
C11 C10 . 1.352(3)
C11 H11 . 0.9300
C10 H10 . 0.9300
C3 C2 . 1.386(2)
C3 H3 . 0.9300
C2 C1 . 1.364(3)
C2 H2 . 0.9300
C1 H1 . 0.9300
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 H1N1 O1W 2_677 0.86 1.80 2.659(2) 176
N2 H2N2 Cl . 0.84(2) 2.59(2) 3.4011(14) 163(2)
O1W H1O1 O1 . 0.868(17) 2.11(2) 2.8465(18) 142(2)
O1W H1O1 N3 . 0.868(17) 2.50(2) 3.2648(19) 148(2)
O2W H2O2 Cl 2_567 0.83(3) 2.41(3) 3.2305(18) 171(3)
O2W H1O2 Cl 1_564 0.85(2) 2.37(2) 3.2102(16) 171(2)
O1W H2O1 O2W . 0.860(19) 1.91(2) 2.764(2) 170(3)
C2 H2 S1 1_556 0.93 2.71 3.6359(19) 179
C3 H3 Cl 1 0.93 2.72 3.629(2) 166
C5 H5 O1 2_677 0.93 2.41 3.207(2) 143
