#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/96/7009604.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_7009604
loop_
_publ_author_name
'Casas, José S.'
'Castiñeiras, Alfonso'
'Rodríguez-Argüelles, María C.'
'Sánchez, Agustín'
'Sordo, José'
'Vázquez-López, Antonia'
'Vázquez-López, Ezequiel M.'
_publ_section_title
;
 Diorganotin(IV) complexes of imidazole-2-carbaldehyde
 thiosemicarbazone (H2ImTSC). The crystal and molecular structures of
 the “free” ligand and of [SnMe2(ImTSC)]
;
_journal_issue                   14
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              2267
_journal_paper_doi               10.1039/b002286l
_journal_year                    2000
_chemical_formula_sum            'C5 H8 N5 O0.5 S'
_chemical_formula_weight         178.22
_chemical_name_systematic
; 
 2-forylimidazole thiosemicarbazone 
;
_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   direct
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.828(9)
_cell_angle_beta                 89.140(10)
_cell_angle_gamma                61.146(9)
_cell_formula_units_Z            4
_cell_length_a                   7.7676(9)
_cell_length_b                   7.8401(9)
_cell_length_c                   15.873(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      9
_cell_volume                     836.44(19)
_computing_cell_refinement       'CAD4-Express (Enraf-Nonius, 1995)'
_computing_data_collection       'CAD4-Express (Enraf-Nonius, 1995)'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CAD4 Enraf-Nonius '
_diffrn_measurement_method       omega/2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3637
_diffrn_reflns_theta_full        67.51
_diffrn_reflns_theta_max         67.51
_diffrn_reflns_theta_min         5.64
_exptl_absorpt_coefficient_mu    3.081
_exptl_absorpt_correction_T_max  0.8612
_exptl_absorpt_correction_T_min  0.2594
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0190(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    isotropic
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0925P)²+0.2192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                2870
_reflns_number_total             2968
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b002286l.txt
_cod_data_source_block           imh
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+0.2192P] 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^)+(0.0925P)^2^+0.2192P] 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        836.44(17)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C5 H8 N5 O0.50 S'
_cod_database_code               7009604
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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32883(7) 0.35254(7) 0.63959(3) 0.0420(2) Uani 1 d . . .
N1 N 0.0086(3) 0.5958(3) 0.71119(14) 0.0437(4) Uani 1 d . . .
H1N1 H -0.017(5) 0.696(6) 0.668(2) 0.072(9) Uiso 1 d . . .
H2N1 H -0.058(4) 0.614(4) 0.7518(19) 0.047(7) Uiso 1 d . . .
N2 N 0.1929(3) 0.2848(3) 0.78607(12) 0.0408(4) Uani 1 d . . .
H2 H 0.301(4) 0.172(5) 0.7945(19) 0.057(7) Uiso 1 d . . .
N3 N 0.0649(2) 0.3373(2) 0.84950(11) 0.0386(4) Uani 1 d . . .
N5 N 0.0114(3) 0.1517(3) 1.06326(12) 0.0457(4) Uani 1 d . . .
N4 N -0.1894(3) 0.4356(3) 0.98311(13) 0.0401(4) Uani 1 d . . .
H4 H -0.227(4) 0.512(4) 0.9435(18) 0.036(7) Uiso 1 d . . .
C1 C 0.1641(3) 0.4193(3) 0.71625(13) 0.0343(4) Uani 1 d . . .
C2 C 0.1102(3) 0.2130(3) 0.91873(14) 0.0397(5) Uani 1 d . . .
H2 H 0.227(4) 0.093(5) 0.9267(19) 0.054(7) Uiso 1 d . . .
C3 C -0.0186(3) 0.2631(3) 0.98779(13) 0.0368(4) Uani 1 d . . .
C5 C -0.1463(4) 0.2567(4) 1.10768(15) 0.0491(5) Uani 1 d . . .
H5 H -0.162(5) 0.211(5) 1.168(2) 0.064(8) Uiso 1 d . . .
C4 C -0.2719(3) 0.4335(4) 1.05877(15) 0.0466(5) Uani 1 d . . .
H4 H -0.391(4) 0.539(5) 1.0709(18) 0.052(7) Uiso 1 d . . .
S11 S 0.59345(7) -0.17363(7) 0.82173(3) 0.0402(2) Uani 1 d . . .
N11 N 0.5417(3) -0.4265(3) 0.74570(14) 0.0459(5) Uani 1 d . . .
H1N2 H 0.584(4) -0.505(4) 0.7888(18) 0.039(6) Uiso 1 d . . .
H2N2 H 0.507(4) -0.461(5) 0.701(2) 0.057(8) Uiso 1 d . . .
N12 N 0.4426(3) -0.1218(3) 0.66699(12) 0.0420(4) Uani 1 d . . .
H12 H 0.430(4) -0.012(4) 0.6622(17) 0.044(7) Uiso 1 d . . .
N13 N 0.3819(2) -0.1801(3) 0.60149(11) 0.0382(4) Uani 1 d . . .
N15 N 0.1490(3) 0.0054(3) 0.39029(12) 0.0456(4) Uani 1 d . . .
N14 N 0.2303(3) -0.2822(3) 0.47099(13) 0.0410(4) Uani 1 d . . .
H14 H 0.261(4) -0.369(4) 0.5156(18) 0.043(6) Uiso 1 d . . .
C11 C 0.5229(3) -0.2491(3) 0.74063(13) 0.0352(4) Uani 1 d . . .
C12 C 0.2987(3) -0.0524(3) 0.53434(14) 0.0387(5) Uani 1 d . . .
H12 H 0.278(4) 0.083(4) 0.5273(18) 0.050(7) Uiso 1 d . . .
C13 C 0.2262(3) -0.1062(3) 0.46540(13) 0.0361(4) Uani 1 d . . .
C15 C 0.1036(4) -0.1065(4) 0.34611(15) 0.0520(6) Uani 1 d . . .
H15 H 0.056(4) -0.058(5) 0.286(2) 0.067(9) Uiso 1 d . . .
C14 C 0.1511(3) -0.2825(4) 0.39510(16) 0.0501(6) Uani 1 d . . .
H14 H 0.137(4) -0.399(4) 0.3882(18) 0.052(7) Uiso 1 d . . .
O1W O 0.3369(3) 0.7930(3) 0.14163(15) 0.0591(5) Uani 1 d . . .
H1W H 0.364(6) 0.840(7) 0.182(3) 0.104(14) Uiso 1 d . . .
H2W H 0.240(7) 0.897(7) 0.113(3) 0.098(13) Uiso 1 d . . .
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'
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
C1 N2 N3 119.48(17) . . ?
C2 N3 N2 117.34(17) . . ?
C3 N5 C5 105.51(19) . . ?
C4 N4 C3 107.1(2) . . ?
N1 C1 N2 118.20(19) . . ?
N1 C1 S1 123.20(17) . . ?
N2 C1 S1 118.60(15) . . ?
N3 C2 C3 119.31(18) . . ?
N5 C3 N4 111.24(19) . . ?
N5 C3 C2 125.87(19) . . ?
N4 C3 C2 122.89(19) . . ?
N5 C5 C4 109.9(2) . . ?
N4 C4 C5 106.3(2) . . ?
C11 N12 N13 119.38(17) . . ?
C12 N13 N12 117.42(17) . . ?
C13 N15 C15 104.64(19) . . ?
C13 N14 C14 106.4(2) . . ?
N11 C11 N12 118.23(19) . . ?
N11 C11 S11 122.92(17) . . ?
N12 C11 S11 118.86(15) . . ?
N13 C12 C13 118.94(18) . . ?
N15 C13 N14 112.07(19) . . ?
N15 C13 C12 125.57(19) . . ?
N14 C13 C12 122.37(19) . . ?
C14 C15 N15 110.3(2) . . ?
N14 C14 C15 106.6(2) . . ?
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 C1 1.697(2) . ?
N1 C1 1.318(3) . ?
N2 C1 1.356(3) . ?
N2 N3 1.365(3) . ?
N3 C2 1.287(3) . ?
N5 C3 1.329(3) . ?
N5 C5 1.357(3) . ?
N4 C4 1.355(3) . ?
N4 C3 1.355(3) . ?
C2 C3 1.438(3) . ?
C5 C4 1.374(4) . ?
S11 C11 1.691(2) . ?
N11 C11 1.317(3) . ?
N12 C11 1.357(3) . ?
N12 N13 1.368(2) . ?
N13 C12 1.284(3) . ?
N15 C13 1.329(3) . ?
N15 C15 1.366(3) . ?
N14 C13 1.354(3) . ?
N14 C14 1.362(3) . ?
C12 C13 1.439(3) . ?
C15 C14 1.363(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N1 N15 0.91(4) 2.12(4) 2.967(3) 155(3) 2_566
N1 H2N1 S11 0.81(3) 2.72(3) 3.443(2) 150(3) 1_465
N2 H2 S11 0.87(3) 2.54(3) 3.4060(19) 174(3) .
N4 H4 S11 0.75(3) 2.68(3) 3.421(2) 170(2) 1_465
N11 H1N2 O1W 0.80(3) 2.16(3) 2.884(3) 150(2) 2_656
N11 H2N2 S1 0.89(3) 2.72(3) 3.500(2) 148(3) 1_545
N12 H12 S1 0.81(3) 2.54(3) 3.3439(19) 170(2) .
N14 H14 S1 0.86(3) 2.57(3) 3.423(2) 173(2) 1_545
O1W H1W S11 0.85(5) 2.78(5) 3.406(2) 131(4) 2_666
O1W H2W N5 0.87(5) 1.98(5) 2.844(3) 171(4) 1_564
