##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
{2-[(2,3-Dichlorophenyl)amino]benzoato-\kO}di-μ₂-ethoxo-octamethyldi-
μ₃-oxo-tetratin(IV)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C38 H50 Cl4 N2 O8 Sn4'
_chemical_formula_sum     'C38 H50 Cl4 N2 O8 Sn4'
_chemical_formula_iupac     '[Sn4 (C H3)8 (C13 H8 Cl2 N O2)2 (C2 H5 O)2 O2]'
_chemical_formula_weight     1279.36
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21 / n'
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     14.0875(6)
_cell_length_b     9.7613(4)
_cell_length_c     17.5858(8)
_cell_angle_alpha     90.00
_cell_angle_beta     100.106(3)
_cell_angle_gamma     90.00
_cell_volume     2380.74(18)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     6140
_cell_measurement_theta_min     2
_cell_measurement_theta_max     20
_cell_measurement_temperature     291.0(3)
_exptl_crystal_description     'needle'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.527
_exptl_crystal_size_mid     0.069
_exptl_crystal_size_min     0.069
_exptl_crystal_density_diffrn     1.785
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1248
_exptl_absorpt_coefficient_mu     2.345
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(X-RED; Stoe & Cie, 1999)'
_exptl_absorpt_correction_T_min     0.518
_exptl_absorpt_correction_T_max     0.894
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     291.0(3)
_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     'Kuma KM4 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     27541
_diffrn_reflns_av_R_equivalents     0.0355
_diffrn_reflns_av_sigmaI/netI     0.0197
_diffrn_reflns_theta_min     3.43
_diffrn_reflns_theta_max     25.10
_diffrn_reflns_theta_full     25.10
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     179
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     32.3
_diffrn_standards_decay_%     0.97
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4230
_reflns_number_gt     3656
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0343
_refine_ls_R_factor_gt     0.0273
_refine_ls_wR_factor_gt     0.0594
_refine_ls_wR_factor_ref     0.0630
_refine_ls_goodness_of_fit_ref     1.149
_refine_ls_restrained_S_all     1.149
_refine_ls_number_reflns     4230
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0294P)²+0.8584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     diffmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     direct
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.104
_refine_diff_density_min     -0.498
_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     'CrysAlis CCD (UNIL IC and Kuma, 2000)'
_computing_cell_refinement     'CrysAlis RED (UNIL IC and Kuma, 2000)'
_computing_data_reduction     'CrysAlis RED'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 for Windows (version
1.062;  Farrugia 1997)
;
_computing_publication_material     'SHELXL97'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Sn1 0.471301(17) 0.03647(2) 0.085414(14) 0.03253(8) Uani d . 1 . . Sn
    O3 0.55398(17) -0.0917(2) 0.03312(13) 0.0367(6) Uani d . 1 . . O
    O4 0.53620(19) -0.1049(3) 0.17197(14) 0.0426(6) Uani d . 1 . . O
    Sn2 0.608001(18) -0.24902(2) 0.102016(14) 0.03517(8) Uani d . 1 . . Sn
    C1 0.7400(3) -0.4772(4) -0.0642(2) 0.0396(9) Uani d . 1 . . C
    C2 0.7974(3) -0.5958(4) -0.0615(2) 0.0441(9) Uani d . 1 . . C
    C3 0.8211(3) -0.6448(5) -0.1307(3) 0.0591(12) Uani d . 1 . . C
    H3 0.8576 -0.7243 -0.1300 0.071 Uiso calc R 1 . . H
    C4 0.7918(4) -0.5788(5) -0.1986(3) 0.0650(13) Uani d . 1 . . C
    H4 0.8081 -0.6140 -0.2438 0.078 Uiso calc R 1 . . H
    C5 0.7385(4) -0.4606(5) -0.2016(3) 0.0635(13) Uani d . 1 . . C
    H5 0.7197 -0.4148 -0.2482 0.076 Uiso calc R 1 . . H
    C6 0.7130(3) -0.4107(5) -0.1347(2) 0.0532(11) Uani d . 1 . . C
    H6 0.6768 -0.3307 -0.1368 0.064 Uiso calc R 1 . . H
    N1 0.8241(3) -0.6661(4) 0.0071(2) 0.0551(9) Uani d . 1 . . N
    H1N 0.7852 -0.6562 0.0435 0.061(13) Uiso d R 1 . . H
    C8 0.9060(3) -0.7469(4) 0.0284(2) 0.0445(10) Uani d . 1 . . C
    C9 0.9049(3) -0.8484(4) 0.0842(2) 0.0403(9) Uani d . 1 . . C
    C10 0.9864(3) -0.9260(4) 0.1103(2) 0.0493(10) Uani d . 1 . . C
    C11 1.0694(3) -0.9083(5) 0.0809(3) 0.0634(13) Uani d . 1 . . C
    H11 1.1231 -0.9631 0.0974 0.076 Uiso calc R 1 . . H
    C12 1.0716(3) -0.8076(5) 0.0265(3) 0.0658(13) Uani d . 1 . . C
    H12 1.1279 -0.7933 0.0068 0.079 Uiso calc R 1 . . H
    C13 0.9917(3) -0.7275(5) 0.0004(3) 0.0584(12) Uani d . 1 . . C
    H13 0.9951 -0.6598 -0.0362 0.070 Uiso calc R 1 . . H
    Cl1 0.80140(8) -0.87167(13) 0.12217(7) 0.0619(3) Uani d . 1 . . Cl
    Cl2 0.98415(9) -1.05157(14) 0.17976(8) 0.0743(4) Uani d . 1 . . Cl
    C7 0.7039(3) -0.4257(4) 0.0053(2) 0.0427(9) Uani d . 1 . . C
    O1 0.66257(19) -0.3075(3) -0.00124(15) 0.0471(7) Uani d . 1 . . O
    O2 0.7110(2) -0.4937(3) 0.06478(17) 0.0583(8) Uani d . 1 . . O
    C14 0.3271(3) -0.0202(5) 0.0867(3) 0.0549(11) Uani d . 1 . . C
    H14A 0.3130 -0.1045 0.0589 0.082 Uiso calc R 1 . . H
    H14B 0.2847 0.0504 0.0628 0.082 Uiso calc R 1 . . H
    H14C 0.3181 -0.0324 0.1392 0.082 Uiso calc R 1 . . H
    C15 0.5441(3) 0.2151(4) 0.1320(3) 0.0582(12) Uani d . 1 . . C
    H15A 0.5985 0.1898 0.1703 0.087 Uiso calc R 1 . . H
    H15B 0.5010 0.2709 0.1553 0.087 Uiso calc R 1 . . H
    H15C 0.5658 0.2657 0.0915 0.087 Uiso calc R 1 . . H
    C16 0.5010(3) -0.3983(5) 0.1015(3) 0.0644(13) Uani d . 1 . . C
    H16A 0.4388 -0.3581 0.0840 0.097 Uiso calc R 1 . . H
    H16B 0.5039 -0.4335 0.1528 0.097 Uiso calc R 1 . . H
    H16C 0.5112 -0.4715 0.0674 0.097 Uiso calc R 1 . . H
    C17 0.7414(3) -0.2255(5) 0.1761(3) 0.0644(13) Uani d . 1 . . C
    H17A 0.7922 -0.2235 0.1462 0.097 Uiso calc R 1 . . H
    H17B 0.7515 -0.3010 0.2116 0.097 Uiso calc R 1 . . H
    H17C 0.7415 -0.1413 0.2043 0.097 Uiso calc R 1 . . H
    C18 0.5096(4) -0.1322(5) 0.2448(2) 0.0657(13) Uani d . 1 . . C
    H18A 0.5361 -0.2202 0.2635 0.079 Uiso calc R 1 . . H
    H18B 0.4400 -0.1384 0.2383 0.079 Uiso calc R 1 . . H
    C19 0.5436(5) -0.0270(6) 0.3027(3) 0.095(2) Uani d . 1 . . C
    H19A 0.6126 -0.0211 0.3099 0.143 Uiso calc R 1 . . H
    H19B 0.5245 -0.0509 0.3508 0.143 Uiso calc R 1 . . H
    H19C 0.5160 0.0598 0.2853 0.143 Uiso calc R 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O3 . 2.036(2) yes
    Sn1 C14 . 2.109(4) yes
    Sn1 C15 . 2.114(4) yes
    Sn1 O3 3_655 2.122(2) yes
    Sn1 O4 . 2.137(2) yes
    O3 Sn1 3_655 2.122(2) no
    Sn2 O3 . 2.020(2) yes
    O4 C18 . 1.421(5) no
    Sn2 O4 . 2.226(2) yes
    Sn2 C16 . 2.096(4) yes
    Sn2 C17 . 2.103(4) yes
    Sn2 O1 . 2.169(3) yes
    C1 C6 . 1.393(5) no
    C1 C2 . 1.409(5) no
    C1 C7 . 1.490(5) no
    C2 N1 . 1.380(5) no
    C2 C3 . 1.401(6) no
    C3 C4 . 1.357(6) no
    C3 H3 . 0.9300 no
    C4 C5 . 1.373(6) no
    C4 H4 . 0.9300 no
    C5 C6 . 1.377(6) no
    C5 H5 . 0.9300 no
    C6 H6 . 0.9300 no
    N1 C8 . 1.394(5) no
    N1 H1N . 0.9187 no
    C8 C13 . 1.393(6) no
    C8 C9 . 1.396(5) no
    C9 C10 . 1.385(5) no
    C9 Cl1 . 1.722(4) no
    C10 C11 . 1.370(6) no
    C10 Cl2 . 1.734(4) no
    C11 C12 . 1.376(7) no
    C11 H11 . 0.9300 no
    C12 C13 . 1.381(6) no
    C12 H12 . 0.9300 no
    C13 H13 . 0.9300 no
    C7 O2 . 1.229(5) no
    C7 O1 . 1.289(4) no
    C14 H14A . 0.9600 no
    C14 H14B . 0.9600 no
    C14 H14C . 0.9600 no
    C15 H15A . 0.9600 no
    C15 H15B . 0.9600 no
    C15 H15C . 0.9600 no
    C16 H16A . 0.9600 no
    C16 H16B . 0.9600 no
    C16 H16C . 0.9600 no
    C17 H17A . 0.9600 no
    C17 H17B . 0.9600 no
    C17 H17C . 0.9600 no
    C18 C19 . 1.466(7) no
    C18 H18A . 0.9700 no
    C18 H18B . 0.9700 no
    C19 H19A . 0.9600 no
    C19 H19B . 0.9600 no
    C19 H19C . 0.9600 no
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
    O3 Sn1 C14 . . 118.17(15) yes
    O3 Sn1 C15 . . 113.89(15) yes
    C14 Sn1 C15 . . 127.94(18) yes
    O3 Sn1 O3 . 3_655 73.92(10) yes
    C14 Sn1 O3 . 3_655 94.68(13) yes
    C15 Sn1 O3 . 3_655 99.06(15) yes
    O3 Sn1 O4 . . 73.61(9) yes
    C14 Sn1 O4 . . 96.61(14) yes
    C15 Sn1 O4 . . 97.98(14) yes
    O3 Sn1 O4 3_655 . 147.22(9) yes
    Sn2 O3 Sn1 . . 112.42(11) no
    Sn2 O3 Sn1 . 3_655 139.72(12) no
    Sn1 O3 Sn1 . 3_655 106.08(10) no
    C18 O4 Sn1 . . 128.0(2) no
    C18 O4 Sn2 . . 126.6(2) no
    Sn1 O4 Sn2 . . 101.16(10) no
    O3 Sn2 C16 . . 109.31(16) yes
    O3 Sn2 C17 . . 119.36(15) yes
    C16 Sn2 C17 . . 129.99(19) yes
    O3 Sn2 O1 . . 81.33(9) yes
    C16 Sn2 O1 . . 100.01(15) yes
    C17 Sn2 O1 . . 97.92(16) yes
    O3 Sn2 O4 . . 72.00(9) yes
    C16 Sn2 O4 . . 92.61(15) yes
    C17 Sn2 O4 . . 91.84(15) yes
    O1 Sn2 O4 . . 153.04(9) yes
    C6 C1 C2 . . 118.6(4) no
    C6 C1 C7 . . 119.6(4) no
    C2 C1 C7 . . 121.8(3) no
    N1 C2 C3 . . 121.3(4) no
    N1 C2 C1 . . 120.3(4) no
    C3 C2 C1 . . 118.3(4) no
    C4 C3 C2 . . 121.4(4) no
    C4 C3 H3 . . 119.3 no
    C2 C3 H3 . . 119.3 no
    C3 C4 C5 . . 120.8(4) no
    C3 C4 H4 . . 119.6 no
    C5 C4 H4 . . 119.6 no
    C4 C5 C6 . . 119.2(4) no
    C4 C5 H5 . . 120.4 no
    C6 C5 H5 . . 120.4 no
    C5 C6 C1 . . 121.7(4) no
    C5 C6 H6 . . 119.2 no
    C1 C6 H6 . . 119.2 no
    C2 N1 C8 . . 127.0(4) no
    C2 N1 H1N . . 116.8 no
    C8 N1 H1N . . 116.1 no
    C13 C8 N1 . . 123.7(4) no
    C13 C8 C9 . . 117.5(4) no
    N1 C8 C9 . . 118.7(4) no
    C10 C9 C8 . . 120.7(4) no
    C10 C9 Cl1 . . 120.5(3) no
    C8 C9 Cl1 . . 118.7(3) no
    C11 C10 C9 . . 121.2(4) no
    C11 C10 Cl2 . . 118.5(3) no
    C9 C10 Cl2 . . 120.3(3) no
    C10 C11 C12 . . 118.6(4) no
    C10 C11 H11 . . 120.7 no
    C12 C11 H11 . . 120.7 no
    C11 C12 C13 . . 121.2(4) no
    C11 C12 H12 . . 119.4 no
    C13 C12 H12 . . 119.4 no
    C12 C13 C8 . . 120.8(4) no
    C12 C13 H13 . . 119.6 no
    C8 C13 H13 . . 119.6 no
    O2 C7 O1 . . 121.9(4) no
    O2 C7 C1 . . 121.8(3) no
    O1 C7 C1 . . 116.3(3) no
    C7 O1 Sn2 . . 112.5(2) no
    Sn1 C14 H14A . . 109.5 no
    Sn1 C14 H14B . . 109.5 no
    H14A C14 H14B . . 109.5 no
    Sn1 C14 H14C . . 109.5 no
    H14A C14 H14C . . 109.5 no
    H14B C14 H14C . . 109.5 no
    Sn1 C15 H15A . . 109.5 no
    Sn1 C15 H15B . . 109.5 no
    H15A C15 H15B . . 109.5 no
    Sn1 C15 H15C . . 109.5 no
    H15A C15 H15C . . 109.5 no
    H15B C15 H15C . . 109.5 no
    Sn2 C16 H16A . . 109.5 no
    Sn2 C16 H16B . . 109.5 no
    H16A C16 H16B . . 109.5 no
    Sn2 C16 H16C . . 109.5 no
    H16A C16 H16C . . 109.5 no
    H16B C16 H16C . . 109.5 no
    Sn2 C17 H17A . . 109.5 no
    Sn2 C17 H17B . . 109.5 no
    H17A C17 H17B . . 109.5 no
    Sn2 C17 H17C . . 109.5 no
    H17A C17 H17C . . 109.5 no
    H17B C17 H17C . . 109.5 no
    O4 C18 C19 . . 112.9(4) no
    O4 C18 H18A . . 109.0 no
    C19 C18 H18A . . 109.0 no
    O4 C18 H18B . . 109.0 no
    C19 C18 H18B . . 109.0 no
    H18A C18 H18B . . 107.8 no
    C18 C19 H19A . . 109.5 no
    C18 C19 H19B . . 109.5 no
    H19A C19 H19B . . 109.5 no
    C18 C19 H19C . . 109.5 no
    H19A C19 H19C . . 109.5 no
    H19B C19 H19C . . 109.5 no
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 C7 O1 Sn2 . . . . 177.5(3) no
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 Cl1 . 0.92 2.51 2.908(4) 107
    N1 H1N O2 . 0.92 1.97 2.639(4) 128
data_global
_journal_date_recd_electronic     2005-07-12
_journal_date_accepted     2005-08-15
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2005
_journal_volume     61
_journal_issue      9
_journal_page_first     m439
_journal_page_last     m441
_journal_paper_category     FM
_journal_coeditor_code     JZ1743
_publ_contact_author_name     'Professor Bartczak, Tadeusz J.'
_publ_contact_author_address
;
Institute of General and Ecological Chemistry
Technical University of Lodz
ul. Zeromskiego 116
90-924 Lodz
Poland
;
_publ_contact_author_email     kruszyna@p.lodz.pl
_publ_contact_author_fax     '(48-42) 631 31 03'
_publ_contact_author_phone     '(48-42) 631 31 37'
_publ_section_title
;
{2-[(2,3-Dichlorophenyl)amino]benzoato-κO}di-μ₂-ethoxooctamethyldi-
μ₃-oxo-tetratin(IV)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kruszynski, Rafal' .
;
Institute of General and Ecological Chemistry
Technical University of Łodz
ul. Zeromskiego 116
90-924 Łodz
Poland
;
    'Bartczak, Tadeusz J.' .
;
Institute of General and Ecological Chemistry
Technical University of Łodz
ul. Zeromskiego 116
90-924 Łodz
Poland
;
