#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/40/2204052.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_2204052
loop_
_publ_author_name
'Venkatraman, Ramaiyer'
'Ray, Paresh Chandra'
'Fronczek, Frank R.'
_publ_section_title
;
 The tetrachlorodiphenylstannate(IV) salt of protonated di-2-pyridyl
 ketone N⁴-ethylthiosemicarbazone
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1035
_journal_page_last               m1037
_journal_paper_doi               10.1107/S1600536804015508
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '2C14 H16 N5 S +, C12 H10 Cl4 Sn 2-'
_chemical_formula_moiety         '2C14 H16 N5 S +, C12 H10 Cl4 Sn 2-'
_chemical_formula_sum            'C40 H42 Cl4 N10 S2 Sn'
_chemical_formula_weight         987.45
_chemical_name_systematic
;
2-[(ethylaminothioylhydrazono)(2-pyridyl)methyl]pyridinium
tetrachlorodiphenylstannate(IV)
;
_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                110.872(9)
_cell_angle_beta                 102.803(7)
_cell_angle_gamma                100.404(7)
_cell_formula_units_Z            1
_cell_length_a                   7.4878(10)
_cell_length_b                   12.009(2)
_cell_length_c                   13.585(2)
_cell_measurement_reflns_used    7524
_cell_measurement_temperature    102
_cell_measurement_theta_max      33.7
_cell_measurement_theta_min      2.5
_cell_volume                     1066.9(3)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL SCALEPACK and DENZO (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      102
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device
'Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)'
_diffrn_measurement_method       'ω scans with κ offsets'
_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  0.022
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34148
_diffrn_reflns_theta_full        33.7
_diffrn_reflns_theta_max         33.7
_diffrn_reflns_theta_min         2.8
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             502
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.87
_refine_diff_density_min         -0.82
_refine_ls_extinction_coef       0.0072(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         8420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.029
_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)+(0.0222P)²+0.6943P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.063
_refine_ls_wR_factor_ref         0.066
_reflns_number_gt                7364
_reflns_number_total             8420
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6238.cif
_cod_data_source_block           I
_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:

'_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2204052
_cod_database_fobs_code          2204052
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Sn1 0.0000 0.5000 0.0000 0.01112(4) Uani d S 1 Sn
Cl1 0.25764(5) 0.42032(3) 0.08791(3) 0.01529(6) Uani d . 1 Cl
Cl2 0.23999(5) 0.60871(3) -0.07324(3) 0.01528(6) Uani d . 1 Cl
S1 0.52760(5) 0.16520(3) 0.35629(3) 0.01867(7) Uani d . 1 S
N1 0.66877(17) 0.63291(11) 0.23120(10) 0.0135(2) Uani d . 1 N
H1N 0.689(3) 0.5640(18) 0.2019(16) 0.016 Uiso d . 1 H
N2 0.7484(2) 0.58289(12) 0.57396(10) 0.0186(2) Uani d . 1 N
N3 0.64295(17) 0.47978(11) 0.33260(10) 0.0136(2) Uani d . 1 N
N4 0.64409(18) 0.39372(11) 0.37465(10) 0.0150(2) Uani d . 1 N
H4N 0.660(3) 0.4163(18) 0.4447(17) 0.018 Uiso d . 1 H
N5 0.5342(2) 0.24590(12) 0.19616(11) 0.0203(2) Uani d . 1 N
H5N 0.556(3) 0.310(2) 0.1784(17) 0.024 Uiso d . 1 H
C1 0.08042(19) 0.66536(13) 0.14971(11) 0.0143(2) Uani d . 1 C
C2 0.1180(2) 0.65826(15) 0.25217(11) 0.0180(3) Uani d . 1 C
H2 0.1158 0.5805 0.2557 0.022 Uiso calc R 1 H
C3 0.1587(2) 0.76431(17) 0.34945(13) 0.0246(3) Uani d . 1 C
H3 0.1858 0.7588 0.4190 0.030 Uiso calc R 1 H
C4 0.1598(2) 0.87768(17) 0.34480(14) 0.0290(4) Uani d . 1 C
H4 0.1840 0.9495 0.4109 0.035 Uiso calc R 1 H
C5 0.1254(2) 0.88641(15) 0.24325(15) 0.0263(3) Uani d . 1 C
H5 0.1288 0.9646 0.2402 0.032 Uiso calc R 1 H
C6 0.0860(2) 0.78074(14) 0.14605(13) 0.0190(3) Uani d . 1 C
H6 0.0627 0.7871 0.0769 0.023 Uiso calc R 1 H
C7 0.70636(19) 0.59739(13) 0.39836(11) 0.0132(2) Uani d . 1 C
C8 0.67596(19) 0.67788(12) 0.33909(11) 0.0124(2) Uani d . 1 C
C9 0.6409(2) 0.79181(13) 0.38432(12) 0.0164(2) Uani d . 1 C
H9 0.6449 0.8260 0.4598 0.020 Uiso calc R 1 H
C10 0.6000(2) 0.85575(14) 0.31859(13) 0.0193(3) Uani d . 1 C
H10 0.5767 0.9342 0.3493 0.023 Uiso calc R 1 H
C11 0.5930(2) 0.80512(15) 0.20838(13) 0.0198(3) Uani d . 1 C
H11 0.5646 0.8481 0.1629 0.024 Uiso calc R 1 H
C12 0.6278(2) 0.69140(14) 0.16563(12) 0.0170(3) Uani d . 1 C
H12 0.6227 0.6549 0.0901 0.020 Uiso calc R 1 H
C13 0.7985(2) 0.65333(13) 0.52051(11) 0.0142(2) Uani d . 1 C
C14 0.9350(2) 0.76891(14) 0.57500(12) 0.0172(3) Uani d . 1 C
H14 0.9678 0.8162 0.5352 0.021 Uiso calc R 1 H
C15 1.0227(2) 0.81401(15) 0.68870(12) 0.0210(3) Uani d . 1 C
H15 1.1176 0.8920 0.7276 0.025 Uiso calc R 1 H
C16 0.9692(2) 0.74321(16) 0.74418(12) 0.0239(3) Uani d . 1 C
H16 1.0254 0.7720 0.8219 0.029 Uiso calc R 1 H
C17 0.8316(3) 0.62918(15) 0.68343(12) 0.0228(3) Uani d . 1 C
H17 0.7945 0.5813 0.7219 0.027 Uiso calc R 1 H
C18 0.5668(2) 0.27008(13) 0.30260(12) 0.0150(2) Uani d . 1 C
C19 0.4663(2) 0.12212(15) 0.10593(13) 0.0237(3) Uani d . 1 C
H19A 0.5029 0.0619 0.1349 0.028 Uiso calc R 1 H
H19B 0.5296 0.1216 0.0491 0.028 Uiso calc R 1 H
C20 0.2530(3) 0.08137(19) 0.05264(18) 0.0375(5) Uani d . 1 C
H20A 0.1896 0.0774 0.1076 0.056 Uiso calc R 1 H
H20B 0.2149 -0.0010 -0.0088 0.056 Uiso calc R 1 H
H20C 0.2158 0.1411 0.0245 0.056 Uiso calc R 1 H
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'
Cl Cl 0.1484 0.1585 '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'
Sn Sn -0.6537 1.4246 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Sn1 C1 2_565 . 180.0 ?
C1 Sn1 Cl1 2_565 2_565 90.82(4) ?
C1 Sn1 Cl1 . 2_565 89.18(4) ?
C1 Sn1 Cl1 2_565 . 89.18(4) ?
C1 Sn1 Cl1 . . 90.82(4) y
Cl1 Sn1 Cl1 2_565 . 180.0 ?
C1 Sn1 Cl2 2_565 2_565 90.56(4) ?
C1 Sn1 Cl2 . 2_565 89.44(4) ?
Cl1 Sn1 Cl2 2_565 2_565 90.515(15) ?
Cl1 Sn1 Cl2 . 2_565 89.484(15) ?
C1 Sn1 Cl2 2_565 . 89.44(4) ?
C1 Sn1 Cl2 . . 90.56(4) y
Cl1 Sn1 Cl2 2_565 . 89.486(15) ?
Cl1 Sn1 Cl2 . . 90.516(15) y
Cl2 Sn1 Cl2 2_565 . 179.9990(10) ?
C12 N1 C8 . . 123.76(12) ?
C12 N1 H1N . . 116.4(13) ?
C8 N1 H1N . . 119.8(13) ?
C17 N2 C13 . . 117.60(14) ?
C7 N3 N4 . . 120.13(12) y
N3 N4 C18 . . 118.33(12) y
N3 N4 H4N . . 119.0(13) ?
C18 N4 H4N . . 120.0(13) ?
C18 N5 C19 . . 125.27(13) y
C18 N5 H5N . . 117.5(14) ?
C19 N5 H5N . . 117.2(14) ?
C2 C1 C6 . . 118.97(13) ?
C2 C1 Sn1 . . 120.23(11) ?
C6 C1 Sn1 . . 120.70(11) ?
C3 C2 C1 . . 120.59(15) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 120.03(16) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 119.95(15) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.09(16) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C1 . . 120.34(15) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
N3 C7 C8 . . 112.66(12) ?
N3 C7 C13 . . 127.07(12) ?
C8 C7 C13 . . 120.26(12) ?
N1 C8 C9 . . 118.06(12) ?
N1 C8 C7 . . 117.48(11) ?
C9 C8 C7 . . 124.29(12) ?
C8 C9 C10 . . 119.60(13) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C11 C10 C9 . . 120.01(14) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C12 C11 C10 . . 119.05(14) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
N1 C12 C11 . . 119.50(13) ?
N1 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
N2 C13 C14 . . 122.40(13) ?
N2 C13 C7 . . 116.02(12) ?
C14 C13 C7 . . 121.51(13) ?
C15 C14 C13 . . 118.93(14) ?
C15 C14 H14 . . 120.5 ?
C13 C14 H14 . . 120.5 ?
C16 C15 C14 . . 118.87(15) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C15 C16 C17 . . 118.40(14) ?
C15 C16 H16 . . 120.8 ?
C17 C16 H16 . . 120.8 ?
N2 C17 C16 . . 123.77(15) ?
N2 C17 H17 . . 118.1 ?
C16 C17 H17 . . 118.1 ?
N5 C18 N4 . . 115.55(13) ?
N5 C18 S1 . . 126.28(11) ?
N4 C18 S1 . . 118.15(11) ?
N5 C19 C20 . . 112.51(14) ?
N5 C19 H19A . . 109.1 ?
C20 C19 H19A . . 109.1 ?
N5 C19 H19B . . 109.1 ?
C20 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.8 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sn1 C1 2_565 2.1424(14) ?
Sn1 C1 . 2.1424(14) y
Sn1 Cl1 2_565 2.5541(4) ?
Sn1 Cl1 . 2.5541(4) y
Sn1 Cl2 2_565 2.6066(4) ?
Sn1 Cl2 . 2.6066(4) y
S1 C18 . 1.6794(15) y
N1 C12 . 1.3356(18) y
N1 C8 . 1.3541(17) y
N1 H1N . 0.840(19) ?
N2 C17 . 1.3356(19) y
N2 C13 . 1.3518(19) y
N3 C7 . 1.2996(18) y
N3 N4 . 1.3476(16) y
N4 C18 . 1.3786(18) y
N4 H4N . 0.86(2) ?
N5 C18 . 1.3243(19) y
N5 C19 . 1.457(2) y
N5 H5N . 0.88(2) ?
C1 C2 . 1.394(2) ?
C1 C6 . 1.398(2) ?
C2 C3 . 1.394(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.384(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.391(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.393(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.4789(19) ?
C7 C13 . 1.4872(19) ?
C8 C9 . 1.3857(19) ?
C9 C10 . 1.390(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.385(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.379(2) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C14 . 1.393(2) ?
C14 C15 . 1.391(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.385(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.388(3) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C19 C20 . 1.506(3) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
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 Cl2 2_665 0.840(19) 2.421(19) 3.2279(13) 161.4(17)
N4 H4N N2 . 0.86(2) 2.01(2) 2.6723(18) 133.0(17)
N5 H5N Cl2 2_665 0.88(2) 2.60(2) 3.3103(15) 138.7(17)
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
C7 N3 N4 C18 . 176.81(13)
Cl1 Sn1 C1 C2 2_565 136.51(11)
Cl1 Sn1 C1 C2 . -43.49(11)
Cl2 Sn1 C1 C2 2_565 45.99(11)
Cl2 Sn1 C1 C2 . -134.01(11)
Cl1 Sn1 C1 C6 2_565 -40.00(11)
Cl1 Sn1 C1 C6 . 140.00(11)
Cl2 Sn1 C1 C6 2_565 -130.52(11)
Cl2 Sn1 C1 C6 . 49.48(11)
C6 C1 C2 C3 . 0.6(2)
Sn1 C1 C2 C3 . -175.98(11)
C1 C2 C3 C4 . 0.8(2)
C2 C3 C4 C5 . -1.8(2)
C3 C4 C5 C6 . 1.4(3)
C4 C5 C6 C1 . 0.1(2)
C2 C1 C6 C5 . -1.0(2)
Sn1 C1 C6 C5 . 175.52(11)
N4 N3 C7 C8 . -174.09(12)
N4 N3 C7 C13 . 5.1(2)
C12 N1 C8 C9 . -0.8(2)
C12 N1 C8 C7 . 174.71(13)
N3 C7 C8 N1 . -27.67(17)
C13 C7 C8 N1 . 153.09(12)
N3 C7 C8 C9 . 147.51(14)
C13 C7 C8 C9 . -31.7(2)
N1 C8 C9 C10 . 0.0(2)
C7 C8 C9 C10 . -175.13(14)
C8 C9 C10 C11 . 0.4(2)
C9 C10 C11 C12 . -0.2(2)
C8 N1 C12 C11 . 1.0(2)
C10 C11 C12 N1 . -0.5(2)
C17 N2 C13 C14 . 1.6(2)
C17 N2 C13 C7 . 178.59(13)
N3 C7 C13 N2 . -27.3(2)
C8 C7 C13 N2 . 151.78(13)
N3 C7 C13 C14 . 149.66(14)
C8 C7 C13 C14 . -31.21(19)
N2 C13 C14 C15 . -0.3(2)
C7 C13 C14 C15 . -177.11(13)
C13 C14 C15 C16 . -0.9(2)
C14 C15 C16 C17 . 0.8(2)
C13 N2 C17 C16 . -1.8(2)
C15 C16 C17 N2 . 0.6(2)
C19 N5 C18 N4 . 175.39(14)
C19 N5 C18 S1 . -3.2(2)
N3 N4 C18 N5 . 13.49(19)
N3 N4 C18 S1 . -167.80(10)
C18 N5 C19 C20 . 95.9(2)
