#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/89/2208905.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_2208905
loop_
_publ_author_name
'Shao-Wen Chen'
'Han-Dong Yin'
_publ_section_title
;
 [3-Methoxy-2-oxidobenzaldehyde
 (2-thienylcarbonyl)hydrazonato]dimethyltin(IV)
;
_journal_coeditor_code           HK2015
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1024
_journal_page_last               m1026
_journal_paper_doi               10.1107/S1600536806011445
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Sn (C H3)2 (C13 H10 N2 O3 S)]'
_chemical_formula_moiety         'C15 H16 N2 O3 S Sn'
_chemical_formula_sum            'C15 H16 N2 O3 S Sn'
_chemical_formula_weight         423.08
_chemical_name_systematic
;
[3-Methoxy-2-oxidobenzaldehyde (2-thienylcarbonyl)hydrazonato]dimethyltin(IV)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.318(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.777(11)
_cell_length_b                   9.670(4)
_cell_length_c                   13.476(6)
_cell_measurement_reflns_used    2678
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.256
_cell_measurement_theta_min      2.258
_cell_volume                     3255(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1996)'
_computing_data_reduction        'SAINT (Bruker, 1996)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1996)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8215
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    1.711
_exptl_absorpt_correction_T_max  0.8896
_exptl_absorpt_correction_T_min  0.4939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.018
_refine_diff_density_min         -0.892
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.145P)²+47.0333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2123
_refine_ls_wR_factor_ref         0.2362
_reflns_number_gt                2074
_reflns_number_total             2858
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2015.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2208905
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
Sn Sn1 0.54243(3) 0.32300(8) 0.54843(5) 0.0490(3) Uani d . 1 . .
N N1 0.5130(4) 0.1323(9) 0.6067(7) 0.052(2) Uani d . 1 . .
N N2 0.5502(4) 0.0284(10) 0.6405(7) 0.056(2) Uani d . 1 . .
O O1 0.4604(3) 0.3862(9) 0.5292(6) 0.0568(19) Uani d . 1 . .
O O2 0.3683(3) 0.5291(10) 0.4933(8) 0.074(3) Uani d . 1 . .
O O3 0.6086(4) 0.1732(8) 0.5871(8) 0.066(2) Uani d . 1 . .
S S1 0.7036(2) -0.0047(5) 0.6673(4) 0.0808(14) Uani d P 0.67 A 1
C C11' 0.7036(2) -0.0047(5) 0.6673(4) 0.0808(14) Uani d P 0.33 A 2
H H11' 0.7198 0.0737 0.6486 0.097 Uiso calc PR 0.33 A 2
C C1 0.4661(4) 0.1053(12) 0.6170(8) 0.052(3) Uani d . 1 . .
H H1 0.4617 0.0196 0.6453 0.062 Uiso calc R 1 . .
C C2 0.4191(5) 0.1919(12) 0.5901(8) 0.052(3) Uani d . 1 . .
C C3 0.4181(4) 0.3270(11) 0.5506(7) 0.046(2) Uani d . 1 . .
C C4 0.3679(4) 0.3984(12) 0.5314(8) 0.053(3) Uani d . 1 . .
C C5 0.3238(5) 0.3373(14) 0.5510(10) 0.064(3) Uani d . 1 . .
H H5 0.2918 0.3861 0.5387 0.077 Uiso calc R 1 . .
C C6 0.3259(5) 0.2036(15) 0.5891(11) 0.070(4) Uani d . 1 . .
H H6 0.2955 0.1626 0.6013 0.084 Uiso calc R 1 . .
C C7 0.3726(5) 0.1338(14) 0.6083(10) 0.064(3) Uani d . 1 . .
H H7 0.3740 0.0445 0.6344 0.076 Uiso calc R 1 . .
C C8 0.3209(7) 0.604(2) 0.4789(16) 0.112(6) Uani d U 1 . .
H H8A 0.3258 0.6940 0.4522 0.168 Uiso calc R 1 . .
H H8B 0.3116 0.6142 0.5432 0.168 Uiso calc R 1 . .
H H8C 0.2928 0.5564 0.4314 0.168 Uiso calc R 1 . .
C C9 0.5970(5) 0.0603(12) 0.6262(8) 0.053(3) Uani d . 1 A .
C C10 0.6412(5) -0.0417(13) 0.6634(8) 0.060(3) Uani d . 1 . .
C C11 0.6321(4) -0.1834(7) 0.7080(7) 0.084(2) Uani d P 0.67 A 1
H H11 0.6009 -0.2231 0.7178 0.101 Uiso calc PR 0.67 A 1
S S1' 0.6321(4) -0.1834(7) 0.7080(7) 0.084(2) Uani d P 0.33 A 2
C C12 0.6874(8) -0.2383(18) 0.7309(13) 0.097(5) Uani d . 1 . .
H H12 0.6953 -0.3278 0.7551 0.116 Uiso calc R 1 A 1
C C13 0.7270(7) -0.151(2) 0.7145(14) 0.095(5) Uani d . 1 A .
H H13 0.7631 -0.1737 0.7293 0.115 Uiso calc R 1 B 1
C C14 0.5347(6) 0.2951(13) 0.3925(9) 0.061(3) Uani d . 1 . .
H H14A 0.5127 0.2157 0.3694 0.092 Uiso calc R 1 . .
H H14B 0.5695 0.2813 0.3802 0.092 Uiso calc R 1 . .
H H14C 0.5184 0.3756 0.3560 0.092 Uiso calc R 1 . .
C C15 0.5735(6) 0.4344(13) 0.6838(9) 0.067(3) Uani d . 1 . .
H H15A 0.5619 0.3922 0.7392 0.101 Uiso calc R 1 . .
H H15B 0.5608 0.5280 0.6752 0.101 Uiso calc R 1 . .
H H15C 0.6119 0.4338 0.6990 0.101 Uiso calc R 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'
O O 0.0106 0.0060 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 Sn1 C15 . 150.0(5) yes
C14 Sn1 O1 . 94.0(4) yes
C15 Sn1 O1 . 96.4(5) yes
C14 Sn1 O3 . 91.6(4) yes
C15 Sn1 O3 . 91.5(5) yes
O1 Sn1 O3 . 153.6(3) yes
C14 Sn1 N1 . 107.2(4) yes
C15 Sn1 N1 . 102.1(4) yes
O1 Sn1 N1 . 82.4(3) yes
O3 Sn1 N1 . 71.4(3) yes
C14 Sn1 O1 5_666 77.3(4) yes
C15 Sn1 O1 5_666 78.0(4) yes
O1 Sn1 O1 5_666 75.7(3) yes
O3 Sn1 O1 5_666 130.7(3) yes
N1 Sn1 O1 5_666 157.9(3) yes
C1 N1 N2 . 114.3(9) ?
C1 N1 Sn1 . 128.8(8) ?
N2 N1 Sn1 . 116.9(7) ?
C9 N2 N1 . 111.7(9) ?
C3 O1 Sn1 . 133.4(7) ?
C4 O2 C8 . 116.6(11) ?
C9 O3 Sn1 . 114.3(7) ?
C13 S1 C10 . 95.2(8) ?
N1 C1 C2 . 127.7(11) ?
N1 C1 H1 . 116.2 ?
C2 C1 H1 . 116.2 ?
C7 C2 C3 . 120.1(11) ?
C7 C2 C1 . 115.1(11) ?
C3 C2 C1 . 124.8(11) ?
O1 C3 C2 . 122.9(10) ?
O1 C3 C4 . 120.5(9) ?
C2 C3 C4 . 116.6(10) ?
O2 C4 C5 . 124.0(11) ?
O2 C4 C3 . 115.1(10) ?
C5 C4 C3 . 121.0(11) ?
C4 C5 C6 . 121.1(12) ?
C4 C5 H5 . 119.4 ?
C6 C5 H5 . 119.4 ?
C7 C6 C5 . 119.3(12) ?
C7 C6 H6 . 120.3 ?
C5 C6 H6 . 120.3 ?
C6 C7 C2 . 121.9(13) ?
C6 C7 H7 . 119.1 ?
C2 C7 H7 . 119.1 ?
O2 C8 H8A . 109.5 ?
O2 C8 H8B . 109.5 ?
H8A C8 H8B . 109.5 ?
O2 C8 H8C . 109.5 ?
H8A C8 H8C . 109.5 ?
H8B C8 H8C . 109.5 ?
O3 C9 N2 . 125.6(11) ?
O3 C9 C10 . 117.5(11) ?
N2 C9 C10 . 116.8(10) ?
C9 C10 C11 . 122.6(11) ?
C9 C10 S1 . 121.9(10) ?
C11 C10 S1 . 115.3(8) ?
C12 C11 C10 . 99.7(10) ?
C12 C11 H11 . 130.2 ?
C10 C11 H11 . 130.2 ?
C13 C12 C11 . 117.1(13) ?
C13 C12 H12 . 121.4 ?
C11 C12 H12 . 121.4 ?
C12 C13 S1 . 112.5(13) ?
C12 C13 H13 . 123.7 ?
S1 C13 H13 . 123.7 ?
Sn1 C14 H14A . 109.5 ?
Sn1 C14 H14B . 109.5 ?
H14A C14 H14B . 109.5 ?
Sn1 C14 H14C . 109.5 ?
H14A C14 H14C . 109.5 ?
H14B C14 H14C . 109.5 ?
Sn1 C15 H15A . 109.5 ?
Sn1 C15 H15B . 109.5 ?
H15A C15 H15B . 109.5 ?
Sn1 C15 H15C . 109.5 ?
H15A C15 H15C . 109.5 ?
H15B C15 H15C . 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 C14 . 2.078(12) yes
Sn1 C15 . 2.099(12) yes
Sn1 O1 . 2.153(7) yes
Sn1 O3 . 2.200(8) yes
Sn1 N1 . 2.210(9) yes
Sn1 O1 5_666 2.995(8) yes
N1 C1 . 1.279(14) yes
N1 N2 . 1.385(13) yes
N2 C9 . 1.303(15) yes
O1 C3 . 1.326(13) yes
O2 C4 . 1.365(14) ?
O2 C8 . 1.39(2) ?
O3 C9 . 1.281(14) yes
S1 C13 . 1.603(19) ?
S1 C10 . 1.635(14) ?
C1 C2 . 1.443(16) ?
C1 H1 . 0.9300 ?
C2 C7 . 1.399(17) ?
C2 C3 . 1.408(15) ?
C3 C4 . 1.434(16) ?
C4 C5 . 1.363(17) ?
C5 C6 . 1.387(18) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.349(19) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.497(16) ?
C10 C11 . 1.538(15) ?
C11 C12 . 1.481(19) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.39(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
_geom_hbond_publ_flag
C8 H8A O3 5_666 0.96 2.29 3.09(2) 140 yes
