##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# 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  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-07-11
_journal_date_accepted     2010-07-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      8
_journal_page_first     m947
_journal_page_last     m947
_journal_paper_category     QM
_journal_coeditor_code     BT5296
_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
;
Chloridomethylphenyl(quinoline-2-carboxylato-κ²N,O)tin(IV)
;
loop_
    _publ_author_name
    _publ_author_address
    'Vafaee, Maryam'
;
Department of Chemistry
General Campus
Shahid Beheshti University
Tehran 1983963113
Iran
;
    'Amini, Mostafa M.'
;
Department of Chemistry
General Campus
Shahid Beheshti University
Tehran 1983963113
Iran
;
    '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
;
Chloridomethylphenyl(quinoline-2-carboxylato-κ²N,O)tin(IV)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H14 Cl N O2 Sn'
_chemical_formula_sum     'C17 H14 Cl N O2 Sn'
_chemical_formula_iupac     '[Sn (C H3) (C6 H5) (C10 H6 N O2) Cl]'
_chemical_formula_weight     418.43
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.6942(5)
_cell_length_b     13.1463(6)
_cell_length_c     11.2733(5)
_cell_angle_alpha     90.00
_cell_angle_beta     93.6890(10)
_cell_angle_gamma     90.00
_cell_volume     1581.60(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9943
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.757
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     1.790
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.6158
_exptl_absorpt_correction_T_max     0.8413
_diffrn_ambient_temperature     100(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 diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14187
_diffrn_reflns_av_R_equivalents     0.0388
_diffrn_reflns_av_sigmaI/netI     0.0350
_diffrn_reflns_theta_min     2.38
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3613
_reflns_number_gt     3433
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0362
_refine_ls_R_factor_gt     0.0351
_refine_ls_wR_factor_gt     0.0942
_refine_ls_wR_factor_ref     0.0955
_refine_ls_goodness_of_fit_ref     1.395
_refine_ls_restrained_S_all     1.395
_refine_ls_number_reflns     3613
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0523P)²+0.1663P] 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     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     1.741
_refine_diff_density_min     -0.937
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0280(15)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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 0.813061(14) 0.776948(11) 0.733408(14) 0.01396(11) Uani d . 1 . .
    Cl Cl1 1.02998(6) 0.75394(6) 0.68330(7) 0.02452(16) Uani d . 1 . .
    O O1 0.77940(15) 0.62981(12) 0.67664(15) 0.0176(3) Uani d . 1 . .
    O O2 0.64876(17) 0.49885(13) 0.64587(16) 0.0217(4) Uani d . 1 . .
    C C1 0.8465(3) 0.77556(17) 0.9205(3) 0.0226(6) Uani d . 1 . .
    H H1A 0.7742 0.8046 0.9575 0.034 Uiso calc R 1 . .
    H H1B 0.9213 0.8160 0.9428 0.034 Uiso calc R 1 . .
    H H1C 0.8596 0.7054 0.9479 0.034 Uiso calc R 1 . .
    C C2 0.7644(2) 0.88296(16) 0.59620(19) 0.0139(4) Uani d . 1 . .
    C C3 0.6502(2) 0.87698(17) 0.52921(19) 0.0161(4) Uani d . 1 . .
    H H3 0.5931 0.8236 0.5435 0.019 Uiso calc R 1 . .
    C C4 0.6195(2) 0.94912(19) 0.4413(2) 0.0193(5) Uani d . 1 . .
    H H4 0.5427 0.9438 0.3945 0.023 Uiso calc R 1 . .
    C C5 0.7010(2) 1.02855(18) 0.4224(2) 0.0203(5) Uani d . 1 . .
    H H5 0.6785 1.0791 0.3647 0.024 Uiso calc R 1 . .
    C C6 0.8157(2) 1.03451(17) 0.4877(2) 0.0197(5) Uani d . 1 . .
    H H6 0.8719 1.0887 0.4742 0.024 Uiso calc R 1 . .
    C C7 0.8479(2) 0.96066(17) 0.5731(2) 0.0167(4) Uani d . 1 . .
    H H7 0.9274 0.9634 0.6158 0.020 Uiso calc R 1 . .
    C C8 0.6698(2) 0.58635(18) 0.6779(2) 0.0163(4) Uani d . 1 . .
    C C9 0.5661(2) 0.65049(17) 0.72434(19) 0.0146(4) Uani d . 1 . .
    C C10 0.4453(2) 0.61082(18) 0.7341(2) 0.0178(4) Uani d . 1 . .
    H H10 0.4255 0.5435 0.7089 0.021 Uiso calc R 1 . .
    C C11 0.3567(2) 0.67171(19) 0.7810(2) 0.0187(5) Uani d . 1 . .
    H H11 0.2747 0.6462 0.7898 0.022 Uiso calc R 1 . .
    C C12 0.3874(3) 0.77218(16) 0.8162(2) 0.0158(5) Uani d . 1 . .
    C C13 0.3008(2) 0.83899(19) 0.8662(2) 0.0193(5) Uani d . 1 . .
    H H13 0.2194 0.8153 0.8813 0.023 Uiso calc R 1 . .
    C C14 0.3339(2) 0.9378(2) 0.8929(2) 0.0207(5) Uani d . 1 . .
    H H14 0.2759 0.9819 0.9271 0.025 Uiso calc R 1 . .
    C C15 0.4546(2) 0.97368(18) 0.86940(19) 0.0186(5) Uani d . 1 . .
    H H15 0.4754 1.0429 0.8845 0.022 Uiso calc R 1 . .
    C C16 0.5418(2) 0.91036(18) 0.82531(19) 0.0172(4) Uani d . 1 . .
    H H16 0.6234 0.9351 0.8126 0.021 Uiso calc R 1 . .
    C C17 0.5105(2) 0.80846(18) 0.79870(19) 0.0140(4) Uani d . 1 . .
    N N1 0.5977(2) 0.74461(18) 0.75477(18) 0.0139(4) 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 C1 . 2.117(3) yes
    Sn1 C2 . 2.122(2) yes
    Sn1 N1 . 2.369(2) yes
    Sn1 O1 . 2.062(2) yes
    Sn1 Cl1 . 2.4414(7) yes
    O1 C8 . 1.305(3) ?
    O2 C8 . 1.222(3) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 C7 . 1.392(3) ?
    C2 C3 . 1.397(3) ?
    C3 C4 . 1.395(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.385(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.392(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.394(3) ?
    C6 H6 . 0.9500 ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.513(3) ?
    C9 N1 . 1.322(3) ?
    C9 C10 . 1.404(3) ?
    C10 C11 . 1.373(3) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.412(4) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.420(3) ?
    C12 C17 . 1.426(3) ?
    C13 C14 . 1.375(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.415(4) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.367(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.408(3) ?
    C16 H16 . 0.9500 ?
    C17 N1 . 1.371(3) ?
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
    O1 Sn1 C1 . . 108.43(8) ?
    O1 Sn1 C2 . . 111.11(7) ?
    C1 Sn1 C2 . . 138.58(9) yes
    O1 Sn1 N1 . . 73.25(7) ?
    C1 Sn1 N1 . . 90.02(10) ?
    C2 Sn1 N1 . . 89.86(8) ?
    O1 Sn1 Cl1 . . 87.79(5) ?
    C1 Sn1 Cl1 . . 97.31(9) ?
    C2 Sn1 Cl1 . . 96.02(6) ?
    N1 Sn1 Cl1 . . 161.00(7) ?
    C8 O1 Sn1 . . 123.13(14) ?
    Sn1 C1 H1A . . 109.5 ?
    Sn1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    Sn1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C7 C2 C3 . . 119.3(2) ?
    C7 C2 Sn1 . . 119.21(16) ?
    C3 C2 Sn1 . . 121.48(16) ?
    C4 C3 C2 . . 120.2(2) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    C5 C4 C3 . . 120.0(2) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 120.2(2) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C5 C6 C7 . . 119.7(2) ?
    C5 C6 H6 . . 120.1 ?
    C7 C6 H6 . . 120.1 ?
    C2 C7 C6 . . 120.5(2) ?
    C2 C7 H7 . . 119.8 ?
    C6 C7 H7 . . 119.8 ?
    O2 C8 O1 . . 123.9(2) ?
    O2 C8 C9 . . 120.1(2) ?
    O1 C8 C9 . . 116.0(2) ?
    N1 C9 C10 . . 123.3(2) ?
    N1 C9 C8 . . 115.5(2) ?
    C10 C9 C8 . . 121.2(2) ?
    C11 C10 C9 . . 118.4(2) ?
    C11 C10 H10 . . 120.8 ?
    C9 C10 H10 . . 120.8 ?
    C10 C11 C12 . . 120.0(2) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C11 C12 C13 . . 123.0(2) ?
    C11 C12 C17 . . 118.3(2) ?
    C13 C12 C17 . . 118.7(2) ?
    C14 C13 C12 . . 120.4(2) ?
    C14 C13 H13 . . 119.8 ?
    C12 C13 H13 . . 119.8 ?
    C13 C14 C15 . . 120.0(2) ?
    C13 C14 H14 . . 120.0 ?
    C15 C14 H14 . . 120.0 ?
    C16 C15 C14 . . 121.1(2) ?
    C16 C15 H15 . . 119.4 ?
    C14 C15 H15 . . 119.4 ?
    C15 C16 C17 . . 119.9(2) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    N1 C17 C16 . . 120.1(2) ?
    N1 C17 C12 . . 120.1(2) ?
    C16 C17 C12 . . 119.8(2) ?
    C9 N1 C17 . . 119.9(2) ?
    C9 N1 Sn1 . . 112.07(16) ?
    C17 N1 Sn1 . . 127.97(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_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 Sn1 O1 C8 . . . . 83.29(19) ?
    C2 Sn1 O1 C8 . . . . -84.14(18) ?
    N1 Sn1 O1 C8 . . . . -0.97(16) ?
    Cl1 Sn1 O1 C8 . . . . -179.74(16) ?
    O1 Sn1 C2 C7 . . . . -133.04(16) ?
    C1 Sn1 C2 C7 . . . . 65.2(2) ?
    N1 Sn1 C2 C7 . . . . 155.02(17) ?
    Cl1 Sn1 C2 C7 . . . . -43.08(17) ?
    O1 Sn1 C2 C3 . . . . 47.46(19) ?
    C1 Sn1 C2 C3 . . . . -114.4(2) ?
    N1 Sn1 C2 C3 . . . . -24.49(18) ?
    Cl1 Sn1 C2 C3 . . . . 137.41(17) ?
    C7 C2 C3 C4 . . . . -1.0(3) ?
    Sn1 C2 C3 C4 . . . . 178.55(16) ?
    C2 C3 C4 C5 . . . . -1.7(3) ?
    C3 C4 C5 C6 . . . . 2.5(3) ?
    C4 C5 C6 C7 . . . . -0.5(3) ?
    C3 C2 C7 C6 . . . . 2.9(3) ?
    Sn1 C2 C7 C6 . . . . -176.62(17) ?
    C5 C6 C7 C2 . . . . -2.2(3) ?
    Sn1 O1 C8 O2 . . . . -179.09(17) ?
    Sn1 O1 C8 C9 . . . . -0.1(3) ?
    O2 C8 C9 N1 . . . . -178.9(2) ?
    O1 C8 C9 N1 . . . . 2.1(3) ?
    O2 C8 C9 C10 . . . . 1.4(3) ?
    O1 C8 C9 C10 . . . . -177.6(2) ?
    N1 C9 C10 C11 . . . . -2.1(3) ?
    C8 C9 C10 C11 . . . . 177.6(2) ?
    C9 C10 C11 C12 . . . . 1.1(4) ?
    C10 C11 C12 C13 . . . . -179.5(2) ?
    C10 C11 C12 C17 . . . . 1.6(4) ?
    C11 C12 C13 C14 . . . . -176.5(2) ?
    C17 C12 C13 C14 . . . . 2.4(3) ?
    C12 C13 C14 C15 . . . . 0.7(3) ?
    C13 C14 C15 C16 . . . . -3.0(3) ?
    C14 C15 C16 C17 . . . . 2.2(3) ?
    C15 C16 C17 N1 . . . . -179.8(2) ?
    C15 C16 C17 C12 . . . . 1.0(3) ?
    C11 C12 C17 N1 . . . . -3.5(3) ?
    C13 C12 C17 N1 . . . . 177.5(2) ?
    C11 C12 C17 C16 . . . . 175.8(2) ?
    C13 C12 C17 C16 . . . . -3.2(3) ?
    C10 C9 N1 C17 . . . . 0.2(3) ?
    C8 C9 N1 C17 . . . . -179.51(19) ?
    C10 C9 N1 Sn1 . . . . 176.98(17) ?
    C8 C9 N1 Sn1 . . . . -2.7(2) ?
    C16 C17 N1 C9 . . . . -176.6(2) ?
    C12 C17 N1 C9 . . . . 2.6(3) ?
    C16 C17 N1 Sn1 . . . . 7.2(3) ?
    C12 C17 N1 Sn1 . . . . -173.62(16) ?
    O1 Sn1 N1 C9 . . . . 2.05(15) ?
    C1 Sn1 N1 C9 . . . . -107.22(17) ?
    C2 Sn1 N1 C9 . . . . 114.19(16) ?
    Cl1 Sn1 N1 C9 . . . . 5.8(3) ?
    O1 Sn1 N1 C17 . . . . 178.5(2) ?
    C1 Sn1 N1 C17 . . . . 69.2(2) ?
    C2 Sn1 N1 C17 . . . . -69.4(2) ?
    Cl1 Sn1 N1 C17 . . . . -177.71(13) ?
