#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/54/2215491.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_2215491
loop_
_publ_author_name
'Vieira, Flaviana T.'
'Menezes, Daniele C.'
'de Lima, Geraldo M.'
'Ardisson, José D.'
'Maia, José R. da S.'
'Speziali, Nivaldo L.'
_publ_section_title
catena-Poly[[trimethyltin(IV)]-μ-2-[(3-oxocyclohex-1-enyl)amino]benzoato-κ²O:O']
_journal_coeditor_code           GW2023
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2587
_journal_page_last               m2587
_journal_paper_doi               10.1107/S1600536807044273
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Sn (C H3)3 (C13 H13 N O3)]'
_chemical_formula_moiety         'C16 H21 N O3 Sn'
_chemical_formula_sum            'C16 H21 N O3 Sn'
_chemical_formula_weight         394.03
_chemical_melting_point          .44E-305
_chemical_name_common
Poly-[trimethyltin-3-{(carboxyphenyl)amino}cyclohexen-2-one]
_chemical_name_systematic
;
<it>catena</it>-Poly[[trimethyltin(IV)]-μ-2-[(3-oxocyclohex-1-
enyl)amino]benzoato-κ²<it>O</it>:<it>O</it>']
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   30.626(5)
_cell_length_b                   12.981(2)
_cell_length_c                   17.164(2)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      12.501
_cell_measurement_theta_min      11.757
_cell_volume                     6823.7(17)
_computing_cell_refinement       'XSCANS (Siemens, 1991)'
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        'XSCANS (Siemens, 1991)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2θ/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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7294
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        4
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.506
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.373
_refine_ls_abs_structure_details 'Flack (1983), with how many Friedel pairs?'
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.740
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.740
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0239
_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)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                2099
_reflns_number_total             2329
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2023.cif
_cod_data_source_block           I
_cod_original_cell_volume        6823.6(19)
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               2215491
_cod_database_fobs_code          2215491
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
Sn Sn 0.411524(8) -0.002008(19) 0.26150(5) 0.05087(14) Uani d . 1
C C1 0.43775(19) 0.1345(4) 0.2137(4) 0.0718(15) Uani d . 1
H H1A 0.4312 0.1915 0.2474 0.108 Uiso calc R 1
H H1B 0.4251 0.1466 0.1634 0.108 Uiso calc R 1
H H1C 0.4688 0.1276 0.2087 0.108 Uiso calc R 1
C C2 0.4509(2) -0.0989(5) 0.3309(4) 0.0772(16) Uani d . 1
H H2A 0.4442 -0.0880 0.3848 0.116 Uiso calc R 1
H H2B 0.4811 -0.0832 0.3218 0.116 Uiso calc R 1
H H2C 0.4454 -0.1695 0.3175 0.116 Uiso calc R 1
C C3 0.3535(2) -0.0753(5) 0.2245(4) 0.089(2) Uani d . 1
H H3A 0.3308 -0.0634 0.2622 0.134 Uiso calc R 1
H H3B 0.3585 -0.1480 0.2196 0.134 Uiso calc R 1
H H3C 0.3447 -0.0477 0.1751 0.134 Uiso calc R 1
O O1 0.38557(11) 0.0726(2) 0.3650(2) 0.0602(8) Uani d . 1
O O2 0.33660(11) 0.1547(2) 0.2914(2) 0.0616(9) Uani d . 1
O O3 0.44514(15) -0.0706(3) 0.1396(2) 0.0771(11) Uani d . 1
C C4 0.35365(15) 0.1367(3) 0.3546(3) 0.0513(10) Uani d . 1
C C5 0.33861(13) 0.1881(3) 0.4283(3) 0.0444(10) Uani d . 1
C C6 0.35136(15) 0.1499(3) 0.5001(3) 0.0558(11) Uani d . 1
H H6A 0.3703 0.0939 0.5021 0.067 Uiso calc R 1
C C7 0.33636(18) 0.1936(5) 0.5696(3) 0.0673(15) Uani d . 1
H H7A 0.3450 0.1670 0.6176 0.081 Uiso calc R 1
C C8 0.3084(2) 0.2772(5) 0.5656(3) 0.0643(15) Uani d . 1
H H8A 0.2977 0.3059 0.6115 0.077 Uiso calc R 1
C C9 0.29629(16) 0.3184(4) 0.4959(3) 0.0561(11) Uani d . 1
H H9A 0.2778 0.3753 0.4950 0.067 Uiso calc R 1
C C10 0.31093(15) 0.2770(4) 0.4268(3) 0.0474(10) Uani d . 1
N N 0.29828(13) 0.3157(3) 0.3544(3) 0.0510(9) Uani d . 1
H H1N 0.3021(18) 0.279(5) 0.310(3) 0.061 Uiso d . 1
C C11 0.45673(14) -0.3331(3) 0.0821(3) 0.0449(10) Uani d . 1
C C12 0.47411(17) -0.3229(4) 0.0014(3) 0.0594(12) Uani d . 1
H H12A 0.4622 -0.3776 -0.0306 0.071 Uiso calc R 1
H H12B 0.5056 -0.3310 0.0026 0.071 Uiso calc R 1
C C13 0.4631(2) -0.2201(4) -0.0352(3) 0.0703(15) Uani d . 1
H H13A 0.4799 -0.2115 -0.0827 0.084 Uiso calc R 1
H H13B 0.4323 -0.2187 -0.0488 0.084 Uiso calc R 1
C C14 0.47305(19) -0.1322(4) 0.0200(4) 0.0665(14) Uani d . 1
H H14A 0.4616 -0.0688 -0.0018 0.080 Uiso calc R 1
H H14B 0.5045 -0.1247 0.0245 0.080 Uiso calc R 1
C C15 0.45398(15) -0.1476(3) 0.1002(3) 0.0528(11) Uani d . 1
C C16 0.44788(16) -0.2510(3) 0.1278(3) 0.0490(11) Uani d . 1
H H16A 0.4376 -0.2617 0.1782 0.059 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'
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'
Sn Sn -0.6537 1.4246 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Sn C2 . . 120.1(3) y
C1 Sn C3 . . 125.5(3) y
C2 Sn C3 . . 112.5(3) y
C1 Sn O1 . . 94.73(19) y
C2 Sn O1 . . 90.8(2) y
C3 Sn O1 . . 97.9(2) y
C1 Sn O3 . . 79.46(19) y
C2 Sn O3 . . 91.4(2) y
C3 Sn O3 . . 86.3(2) y
O1 Sn O3 . . 174.13(13) y
Sn C1 H1A . . 109.5 ?
Sn C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
Sn C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
Sn C2 H2A . . 109.5 ?
Sn C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
Sn C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
Sn C3 H3A . . 109.5 ?
Sn C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
Sn C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C4 O1 Sn . . 116.7(3) ?
C15 O3 Sn . . 146.8(4) ?
O2 C4 O1 . . 124.4(4) ?
O2 C4 C5 . . 122.0(4) ?
O1 C4 C5 . . 113.6(4) ?
C6 C5 C10 . . 118.1(4) ?
C6 C5 C4 . . 120.2(4) ?
C10 C5 C4 . . 121.6(4) ?
C5 C6 C7 . . 121.4(4) ?
C5 C6 H6A . . 119.3 ?
C7 C6 H6A . . 119.3 ?
C8 C7 C6 . . 118.6(5) ?
C8 C7 H7A . . 120.7 ?
C6 C7 H7A . . 120.7 ?
C9 C8 C7 . . 121.3(5) ?
C9 C8 H8A . . 119.3 ?
C7 C8 H8A . . 119.3 ?
C8 C9 C10 . . 121.0(5) ?
C8 C9 H9A . . 119.5 ?
C10 C9 H9A . . 119.5 ?
C9 C10 N . . 122.4(5) ?
C9 C10 C5 . . 119.5(5) ?
N C10 C5 . . 118.1(4) ?
C11 N C10 16 . 128.5(4) y
C11 N H1N 16 . 106(4) ?
C10 N H1N . . 122(4) ?
C16 C11 N . 12_544 124.6(4) ?
C16 C11 C12 . . 122.8(4) ?
N C11 C12 12_544 . 112.6(4) ?
C11 C12 C13 . . 112.7(4) ?
C11 C12 H12A . . 109.1 ?
C13 C12 H12A . . 109.1 ?
C11 C12 H12B . . 109.1 ?
C13 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
C14 C13 C12 . . 111.0(5) ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13B . . 109.4 ?
C12 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C13 C14 C15 . . 113.1(4) ?
C13 C14 H14A . . 109.0 ?
C15 C14 H14A . . 109.0 ?
C13 C14 H14B . . 109.0 ?
C15 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
O3 C15 C16 . . 123.1(5) ?
O3 C15 C14 . . 118.5(4) ?
C16 C15 C14 . . 118.4(4) ?
C11 C16 C15 . . 121.3(4) ?
C11 C16 H16A . . 119.4 ?
C15 C16 H16A . . 119.4 ?
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
Sn C1 . 2.112(5) y
Sn C2 . 2.111(6) y
Sn C3 . 2.113(6) y
Sn O1 . 2.174(4) y
Sn O3 . 2.496(4) y
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
O1 C4 . 1.296(5) ?
O2 C4 . 1.227(6) ?
O3 C15 . 1.237(6) ?
C4 C5 . 1.503(7) ?
C5 C6 . 1.384(7) ?
C5 C10 . 1.432(7) ?
C6 C7 . 1.400(8) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.384(9) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.362(8) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.377(7) ?
C9 H9A . 0.9300 ?
C10 N . 1.396(7) y
N C11 16 1.376(6) y
N H1N . 0.91(6) ?
C11 C16 . 1.351(6) ?
C11 N 12_544 1.376(6) ?
C11 C12 . 1.489(7) ?
C12 C13 . 1.513(8) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.515(8) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.508(8) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.436(6) ?
C16 H16A . 0.9300 ?
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
N H1N O2 0.91(6) 1.96(6) 2.631(5) 129(5)
