##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-05-27
_journal_date_accepted     2009-05-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      7
_journal_page_first     m721
_journal_page_last     m721
_journal_paper_category     QM
_journal_coeditor_code     TK2469
_publ_contact_author
;
Dr. Seik Weng Ng
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
(2-Amido-3-oxidopyridinium-κ²N,O)dibenzylchloridotin(IV)
;
loop_
    _publ_author_name
    _publ_author_address
    'Tan, Chui Lian'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Lo, Kong Mun'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(2-Amido-3-oxidopyridinium-κ²N,O)dibenzylchloridotin(IV)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H19 Cl N2 O Sn'
_chemical_formula_sum     'C19 H19 Cl N2 O Sn'
_chemical_formula_iupac     '[Sn (C7 H7)2 (C5 H5 N2 O) Cl]'
_chemical_formula_weight     445.50
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_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'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     11.04570(10)
_cell_length_b     16.8447(2)
_cell_length_c     19.1227(2)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3558.00(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9941
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     28.2
_cell_measurement_temperature     133(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     'pale-yellow'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.663
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1776
_exptl_absorpt_coefficient_mu     1.594
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.640
_exptl_absorpt_correction_T_max     0.746
_diffrn_ambient_temperature     133(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     32398
_diffrn_reflns_av_R_equivalents     0.025
_diffrn_reflns_av_sigmaI/netI     0.014
_diffrn_reflns_theta_min     2.1
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     4086
_reflns_number_gt     3434
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.028
_refine_ls_R_factor_gt     0.021
_refine_ls_wR_factor_gt     0.051
_refine_ls_wR_factor_ref     0.054
_refine_ls_goodness_of_fit_ref     1.01
_refine_ls_restrained_S_all     1.01
_refine_ls_number_reflns     4086
_refine_ls_number_parameters     225
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0279P)²+2.1692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.58
_refine_diff_density_min     -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2009)'
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 0.497920(10) 0.547145(7) 0.324875(6) 0.01725(5) Uani d . 1 . .
    Cl Cl1 0.65272(4) 0.45738(3) 0.37607(3) 0.02492(10) Uani d . 1 . .
    O O1 0.40585(10) 0.64531(8) 0.26870(6) 0.0207(3) Uani d . 1 . .
    N N1 0.68659(13) 0.70633(9) 0.19394(8) 0.0185(3) Uani d D 1 . .
    H H1 0.7626(10) 0.6937(12) 0.2015(11) 0.024(5) Uiso d D 1 . .
    N N2 0.63839(13) 0.61218(9) 0.28027(8) 0.0183(3) Uani d D 1 . .
    H H2 0.7151(10) 0.6008(13) 0.2832(12) 0.033(6) Uiso d D 1 . .
    C C1 0.43387(17) 0.46293(11) 0.24812(10) 0.0224(4) Uani d . 1 . .
    H H1A 0.4448 0.4079 0.2653 0.027 Uiso calc R 1 . .
    H H1B 0.3469 0.4716 0.2383 0.027 Uiso calc R 1 . .
    C C2 0.50788(15) 0.47652(12) 0.18346(10) 0.0212(4) Uani d . 1 . .
    C C3 0.46973(18) 0.53013(12) 0.13232(10) 0.0230(4) Uani d . 1 . .
    H H3 0.3931 0.5552 0.1369 0.028 Uiso calc R 1 . .
    C C4 0.54191(19) 0.54737(12) 0.07487(11) 0.0261(4) Uani d . 1 . .
    H H4 0.5147 0.5844 0.0408 0.031 Uiso calc R 1 . .
    C C5 0.65348(18) 0.51080(12) 0.06696(10) 0.0277(4) Uani d . 1 . .
    H H5 0.7032 0.5228 0.0278 0.033 Uiso calc R 1 . .
    C C6 0.69168(18) 0.45658(12) 0.11679(11) 0.0274(4) Uani d . 1 . .
    H H6 0.7676 0.4308 0.1114 0.033 Uiso calc R 1 . .
    C C7 0.62000(17) 0.43961(12) 0.17456(10) 0.0238(4) Uani d . 1 . .
    H H7 0.6476 0.4025 0.2084 0.029 Uiso calc R 1 . .
    C C8 0.44732(17) 0.60092(12) 0.42300(10) 0.0229(4) Uani d . 1 . .
    H H8A 0.3655 0.6246 0.4198 0.027 Uiso calc R 1 . .
    H H8B 0.4474 0.5609 0.4609 0.027 Uiso calc R 1 . .
    C C9 0.54035(17) 0.66398(11) 0.43697(9) 0.0216(4) Uani d . 1 . .
    C C10 0.65205(17) 0.64382(11) 0.46612(9) 0.0234(4) Uani d . 1 . .
    H H10 0.6665 0.5907 0.4805 0.028 Uiso calc R 1 . .
    C C11 0.74193(18) 0.70028(12) 0.47429(10) 0.0271(4) Uani d . 1 . .
    H H11 0.8177 0.6854 0.4938 0.033 Uiso calc R 1 . .
    C C12 0.72242(19) 0.77828(12) 0.45420(11) 0.0286(4) Uani d . 1 . .
    H H12 0.7841 0.8170 0.4602 0.034 Uiso calc R 1 . .
    C C13 0.6121(2) 0.79920(12) 0.42533(11) 0.0301(4) Uani d . 1 . .
    H H13 0.5978 0.8526 0.4116 0.036 Uiso calc R 1 . .
    C C14 0.52218(18) 0.74232(12) 0.41639(11) 0.0265(4) Uani d . 1 . .
    H H14 0.4472 0.7572 0.3959 0.032 Uiso calc R 1 . .
    C C15 0.48011(15) 0.68662(11) 0.22755(10) 0.0179(4) Uani d . 1 . .
    C C16 0.44615(17) 0.74253(11) 0.17952(10) 0.0225(4) Uani d . 1 . .
    H H16 0.3632 0.7565 0.1748 0.027 Uiso calc R 1 . .
    C C17 0.53422(18) 0.77968(12) 0.13674(10) 0.0246(4) Uani d . 1 . .
    H H17 0.5103 0.8175 0.1026 0.030 Uiso calc R 1 . .
    C C18 0.65246(17) 0.76107(11) 0.14473(10) 0.0232(4) Uani d . 1 . .
    H H18 0.7119 0.7859 0.1162 0.028 Uiso calc R 1 . .
    C C19 0.60653(15) 0.66784(10) 0.23445(9) 0.0158(3) Uani d . 1 . .
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 N2 . 2.0821(15) ?
    Sn1 C8 . 2.1573(19) ?
    Sn1 C1 . 2.1604(18) ?
    Sn1 O1 . 2.2187(12) ?
    Sn1 Cl1 . 2.4836(4) ?
    O1 C15 . 1.333(2) ?
    N1 C19 . 1.343(2) ?
    N1 C18 . 1.370(2) ?
    N1 H1 . 0.878(9) ?
    N2 C19 . 1.331(2) ?
    N2 H2 . 0.871(9) ?
    C1 C2 . 1.500(3) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C7 . 1.396(3) ?
    C2 C3 . 1.396(3) ?
    C3 C4 . 1.388(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.386(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.386(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.389(3) ?
    C6 H6 . 0.9500 ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.502(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C14 . 1.392(3) ?
    C9 C10 . 1.396(3) ?
    C10 C11 . 1.384(3) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.386(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.383(3) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.391(3) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.368(3) ?
    C15 C19 . 1.438(2) ?
    C16 C17 . 1.417(3) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.352(3) ?
    C17 H17 . 0.9500 ?
    C18 H18 . 0.9500 ?
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
    N2 Sn1 C8 . . 109.18(7) ?
    N2 Sn1 C1 . . 108.13(7) ?
    C8 Sn1 C1 . . 141.43(7) ?
    N2 Sn1 O1 . . 75.58(5) ?
    C8 Sn1 O1 . . 89.40(6) ?
    C1 Sn1 O1 . . 90.59(6) ?
    N2 Sn1 Cl1 . . 88.21(4) ?
    C8 Sn1 Cl1 . . 95.23(5) ?
    C1 Sn1 Cl1 . . 95.36(5) ?
    O1 Sn1 Cl1 . . 163.77(3) ?
    C15 O1 Sn1 . . 113.14(10) ?
    C19 N1 C18 . . 122.68(15) ?
    C19 N1 H1 . . 114.7(14) ?
    C18 N1 H1 . . 122.6(14) ?
    C19 N2 Sn1 . . 116.32(11) ?
    C19 N2 H2 . . 117.0(15) ?
    Sn1 N2 H2 . . 125.7(15) ?
    C2 C1 Sn1 . . 106.34(12) ?
    C2 C1 H1A . . 110.5 ?
    Sn1 C1 H1A . . 110.5 ?
    C2 C1 H1B . . 110.5 ?
    Sn1 C1 H1B . . 110.5 ?
    H1A C1 H1B . . 108.7 ?
    C7 C2 C3 . . 118.06(18) ?
    C7 C2 C1 . . 121.07(18) ?
    C3 C2 C1 . . 120.77(17) ?
    C4 C3 C2 . . 121.08(18) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 120.27(19) ?
    C5 C4 H4 . . 119.9 ?
    C3 C4 H4 . . 119.9 ?
    C6 C5 C4 . . 119.25(19) ?
    C6 C5 H5 . . 120.4 ?
    C4 C5 H5 . . 120.4 ?
    C5 C6 C7 . . 120.60(18) ?
    C5 C6 H6 . . 119.7 ?
    C7 C6 H6 . . 119.7 ?
    C6 C7 C2 . . 120.73(19) ?
    C6 C7 H7 . . 119.6 ?
    C2 C7 H7 . . 119.6 ?
    C9 C8 Sn1 . . 105.93(12) ?
    C9 C8 H8A . . 110.6 ?
    Sn1 C8 H8A . . 110.6 ?
    C9 C8 H8B . . 110.6 ?
    Sn1 C8 H8B . . 110.6 ?
    H8A C8 H8B . . 108.7 ?
    C14 C9 C10 . . 118.10(18) ?
    C14 C9 C8 . . 121.45(17) ?
    C10 C9 C8 . . 120.25(17) ?
    C11 C10 C9 . . 120.81(18) ?
    C11 C10 H10 . . 119.6 ?
    C9 C10 H10 . . 119.6 ?
    C10 C11 C12 . . 120.59(19) ?
    C10 C11 H11 . . 119.7 ?
    C12 C11 H11 . . 119.7 ?
    C13 C12 C11 . . 119.29(19) ?
    C13 C12 H12 . . 120.4 ?
    C11 C12 H12 . . 120.4 ?
    C12 C13 C14 . . 120.17(19) ?
    C12 C13 H13 . . 119.9 ?
    C14 C13 H13 . . 119.9 ?
    C13 C14 C9 . . 121.04(19) ?
    C13 C14 H14 . . 119.5 ?
    C9 C14 H14 . . 119.5 ?
    O1 C15 C16 . . 125.95(16) ?
    O1 C15 C19 . . 115.38(15) ?
    C16 C15 C19 . . 118.65(16) ?
    C15 C16 C17 . . 120.23(17) ?
    C15 C16 H16 . . 119.9 ?
    C17 C16 H16 . . 119.9 ?
    C18 C17 C16 . . 119.72(18) ?
    C18 C17 H17 . . 120.1 ?
    C16 C17 H17 . . 120.1 ?
    C17 C18 N1 . . 119.96(17) ?
    C17 C18 H18 . . 120.0 ?
    N1 C18 H18 . . 120.0 ?
    N2 C19 N1 . . 123.10(15) ?
    N2 C19 C15 . . 118.18(15) ?
    N1 C19 C15 . . 118.71(16) ?
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_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N2 Sn1 O1 C15 . . . . 9.88(12) ?
    C8 Sn1 O1 C15 . . . . 119.87(12) ?
    C1 Sn1 O1 C15 . . . . -98.71(12) ?
    Cl1 Sn1 O1 C15 . . . . 13.0(2) ?
    C8 Sn1 N2 C19 . . . . -94.25(14) ?
    C1 Sn1 N2 C19 . . . . 75.77(14) ?
    O1 Sn1 N2 C19 . . . . -10.04(12) ?
    Cl1 Sn1 N2 C19 . . . . 170.83(13) ?
    N2 Sn1 C1 C2 . . . . -1.11(14) ?
    C8 Sn1 C1 C2 . . . . 163.69(12) ?
    O1 Sn1 C1 C2 . . . . 73.91(13) ?
    Cl1 Sn1 C1 C2 . . . . -90.98(12) ?
    Sn1 C1 C2 C7 . . . . 85.78(19) ?
    Sn1 C1 C2 C3 . . . . -90.42(18) ?
    C7 C2 C3 C4 . . . . -1.1(3) ?
    C1 C2 C3 C4 . . . . 175.23(18) ?
    C2 C3 C4 C5 . . . . 0.6(3) ?
    C3 C4 C5 C6 . . . . 0.4(3) ?
    C4 C5 C6 C7 . . . . -0.8(3) ?
    C5 C6 C7 C2 . . . . 0.3(3) ?
    C3 C2 C7 C6 . . . . 0.7(3) ?
    C1 C2 C7 C6 . . . . -175.64(17) ?
    N2 Sn1 C8 C9 . . . . -8.06(14) ?
    C1 Sn1 C8 C9 . . . . -172.75(12) ?
    O1 Sn1 C8 C9 . . . . -82.56(12) ?
    Cl1 Sn1 C8 C9 . . . . 81.86(12) ?
    Sn1 C8 C9 C14 . . . . 93.23(18) ?
    Sn1 C8 C9 C10 . . . . -81.55(18) ?
    C14 C9 C10 C11 . . . . 0.1(3) ?
    C8 C9 C10 C11 . . . . 175.01(17) ?
    C9 C10 C11 C12 . . . . 0.6(3) ?
    C10 C11 C12 C13 . . . . -0.4(3) ?
    C11 C12 C13 C14 . . . . -0.3(3) ?
    C12 C13 C14 C9 . . . . 0.9(3) ?
    C10 C9 C14 C13 . . . . -0.8(3) ?
    C8 C9 C14 C13 . . . . -175.65(18) ?
    Sn1 O1 C15 C16 . . . . 170.06(16) ?
    Sn1 O1 C15 C19 . . . . -8.36(19) ?
    O1 C15 C16 C17 . . . . -177.14(17) ?
    C19 C15 C16 C17 . . . . 1.2(3) ?
    C15 C16 C17 C18 . . . . -1.6(3) ?
    C16 C17 C18 N1 . . . . 0.2(3) ?
    C19 N1 C18 C17 . . . . 1.7(3) ?
    Sn1 N2 C19 N1 . . . . -169.87(13) ?
    Sn1 N2 C19 C15 . . . . 9.3(2) ?
    C18 N1 C19 N2 . . . . 177.05(17) ?
    C18 N1 C19 C15 . . . . -2.1(3) ?
    O1 C15 C19 N2 . . . . -0.1(2) ?
    C16 C15 C19 N2 . . . . -178.61(17) ?
    O1 C15 C19 N1 . . . . 179.10(15) ?
    C16 C15 C19 N1 . . . . 0.6(3) ?
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
    N1 H1 O1 6_656 0.880(10)
                           1.870(10)
                                   2.726(2) 165(2) yes
