#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/26/2212623.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_2212623
loop_
_publ_author_name
'Yawen Han'
'Rufen Zhang'
'Daqi Wang'
_publ_section_title
catena-Poly[[dibutyltin(IV)]-μ-3,4,5,6-tetrafluorobenzene-1,2-dicarboxylato-κ⁴O¹,O^1'^:O²,O^2'^]
_journal_coeditor_code           KP2085
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m776
_journal_page_last               m777
_journal_paper_doi               10.1107/S1600536807006940
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Sn (C4 H9)2 (C8 F4 O4)]'
_chemical_formula_moiety         'C16 H18 F4 O4 Sn'
_chemical_formula_sum            'C16 H18 F4 O4 Sn'
_chemical_formula_weight         468.99
_chemical_name_systematic
;
catena-Poly[[dibutyltin(IV)]-μ-3,4,5,6-tetrafluorobenzene-1,2-dicarboxylato-
κ⁴O¹,O^1'^:O²,O^2'^]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.732(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8470(17)
_cell_length_b                   17.733(3)
_cell_length_c                   11.146(2)
_cell_measurement_reflns_used    3138
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.624
_cell_measurement_theta_min      2.219
_cell_volume                     1873.4(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9445
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.418
_exptl_absorpt_correction_T_max  0.8154
_exptl_absorpt_correction_T_min  0.7363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.967
_refine_diff_density_min         -1.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     376
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0554
_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)+(0.121P)²+0.7607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1838
_reflns_number_gt                2125
_reflns_number_total             3238
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2085.cif
_cod_data_source_block           I
_cod_original_cell_volume        1873.3(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212623
_cod_database_fobs_code          2212623
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Sn Sn1 0.53223(7) 0.19966(3) 0.14262(5) 0.0682(3) Uani d U 1
F F1 0.3152(7) -0.0370(3) 0.2338(5) 0.1068(19) Uani d . 1
F F2 0.1551(7) -0.1018(3) 0.3641(6) 0.1124(19) Uani d . 1
F F3 0.1259(6) -0.0376(3) 0.5742(6) 0.1044(18) Uani d . 1
F F4 0.2610(7) 0.0900(3) 0.6573(5) 0.1004(18) Uani d . 1
O O1 0.4000(6) 0.1622(3) 0.2470(4) 0.0653(13) Uani d . 1
O O2 0.5585(7) 0.0710(3) 0.2748(5) 0.0831(16) Uani d . 1
O O3 0.5552(6) 0.1795(3) 0.5122(5) 0.0715(14) Uani d . 1
O O4 0.3898(7) 0.2097(3) 0.6020(5) 0.0747(15) Uani d . 1
C C1 0.4561(10) 0.0987(5) 0.2964(7) 0.0700(14) Uani d U 1
C C2 0.3763(9) 0.0620(4) 0.3786(6) 0.0630(15) Uani d U 1
C C3 0.3062(9) -0.0040(4) 0.3392(7) 0.0701(16) Uani d U 1
C C4 0.2217(9) -0.0372(4) 0.4045(7) 0.0733(17) Uani d U 1
C C5 0.2073(9) -0.0040(5) 0.5108(8) 0.0712(16) Uani d U 1
C C6 0.2767(9) 0.0609(4) 0.5513(7) 0.0683(16) Uani d U 1
C C7 0.3607(8) 0.0950(4) 0.4875(6) 0.0596(15) Uani d U 1
C C8 0.4430(10) 0.1659(4) 0.5342(7) 0.0650(15) Uani d U 1
C C9 0.7078(11) 0.2375(6) 0.2756(10) 0.098(2) Uani d DU 1
H H9A 0.7105 0.2921 0.2810 0.118 Uiso calc R 1
H H9B 0.7139 0.2163 0.3570 0.118 Uiso calc R 1
C C10 0.8273(12) 0.2053(7) 0.2183(13) 0.121(3) Uani d DU 1
H H10A 0.8120 0.1521 0.1996 0.146 Uiso calc R 1
H H10B 0.8263 0.2318 0.1418 0.146 Uiso calc R 1
C C11 0.9663(12) 0.2172(8) 0.3142(14) 0.139(3) Uani d DU 1
H H11A 0.9694 0.1882 0.3888 0.167 Uiso calc R 1
H H11B 0.9787 0.2701 0.3368 0.167 Uiso calc R 1
C C12 1.0845(16) 0.1906(9) 0.2558(19) 0.179(6) Uani d DU 1
H H12A 1.1750 0.2026 0.3112 0.268 Uiso calc R 1
H H12B 1.0742 0.2158 0.1775 0.268 Uiso calc R 1
H H12C 1.0775 0.1371 0.2425 0.268 Uiso calc R 1
C C13 0.4925(10) 0.1354(5) -0.0233(9) 0.0896(19) Uani d DU 1
H H13A 0.4703 0.1697 -0.0938 0.108 Uiso calc R 1
H H13B 0.5782 0.1088 -0.0244 0.108 Uiso calc R 1
C C14 0.3719(9) 0.0775(5) -0.0410(8) 0.0891(19) Uani d DU 1
H H14A 0.3714 0.0455 -0.1117 0.107 Uiso calc R 1
H H14B 0.3891 0.0457 0.0324 0.107 Uiso calc R 1
C C15 0.2331(10) 0.1137(6) -0.0617(10) 0.104(2) Uani d DU 1
H H15A 0.2189 0.1482 -0.1315 0.124 Uiso calc R 1
H H15B 0.2317 0.1430 0.0115 0.124 Uiso calc R 1
C C16 0.1109(12) 0.0563(8) -0.0883(12) 0.140(4) Uani d DU 1
H H16A 0.0229 0.0826 -0.1021 0.210 Uiso calc R 1
H H16B 0.1227 0.0231 -0.0182 0.210 Uiso calc R 1
H H16C 0.1113 0.0274 -0.1611 0.210 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'
F F 0.0171 0.0103 '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
C9 Sn1 O1 . . 103.5(3) yes
C9 Sn1 O4 . 4_565 106.7(3) yes
O1 Sn1 O4 . 4_565 83.2(2) yes
C9 Sn1 C13 . . 136.4(4) yes
O1 Sn1 C13 . . 108.8(3) yes
O4 Sn1 C13 4_565 . 105.6(3) yes
C9 Sn1 O2 . . 86.8(3) yes
O1 Sn1 O2 . . 53.40(19) yes
O4 Sn1 O2 4_565 . 136.6(2) yes
C13 Sn1 O2 . . 89.4(3) yes
C1 O1 Sn1 . . 104.7(5) ?
C1 O2 Sn1 . . 78.6(4) ?
C8 O4 Sn1 . 4_566 103.5(6) ?
O2 C1 O1 . . 123.2(7) yes
O2 C1 C2 . . 123.2(7) ?
O1 C1 C2 . . 113.5(7) ?
C3 C2 C7 . . 118.2(7) ?
C3 C2 C1 . . 118.4(7) ?
C7 C2 C1 . . 123.1(7) ?
F1 C3 C2 . . 120.5(7) ?
F1 C3 C4 . . 118.1(7) ?
C2 C3 C4 . . 121.4(7) ?
F2 C4 C5 . . 120.4(8) ?
F2 C4 C3 . . 120.0(8) ?
C5 C4 C3 . . 119.6(8) ?
F3 C5 C6 . . 121.4(8) ?
F3 C5 C4 . . 118.9(8) ?
C6 C5 C4 . . 119.7(8) ?
F4 C6 C5 . . 117.1(7) ?
F4 C6 C7 . . 121.3(7) ?
C5 C6 C7 . . 121.6(7) ?
C6 C7 C2 . . 119.4(7) ?
C6 C7 C8 . . 122.2(7) ?
C2 C7 C8 . . 118.3(7) ?
O3 C8 O4 . . 122.3(7) yes
O3 C8 C7 . . 121.7(7) ?
O4 C8 C7 . . 116.0(8) ?
C10 C9 Sn1 . . 99.4(7) ?
C10 C9 H9A . . 111.9 ?
Sn1 C9 H9A . . 111.9 ?
C10 C9 H9B . . 111.9 ?
Sn1 C9 H9B . . 111.9 ?
H9A C9 H9B . . 109.6 ?
C11 C10 C9 . . 107.1(10) ?
C11 C10 H10A . . 110.3 ?
C9 C10 H10A . . 110.3 ?
C11 C10 H10B . . 110.3 ?
C9 C10 H10B . . 110.3 ?
H10A C10 H10B . . 108.6 ?
C10 C11 C12 . . 107.5(12) ?
C10 C11 H11A . . 110.2 ?
C12 C11 H11A . . 110.2 ?
C10 C11 H11B . . 110.2 ?
C12 C11 H11B . . 110.2 ?
H11A C11 H11B . . 108.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 Sn1 . . 115.1(6) ?
C14 C13 H13A . . 108.5 ?
Sn1 C13 H13A . . 108.5 ?
C14 C13 H13B . . 108.5 ?
Sn1 C13 H13B . . 108.5 ?
H13A C13 H13B . . 107.5 ?
C15 C14 C13 . . 112.4(8) ?
C15 C14 H14A . . 109.1 ?
C13 C14 H14A . . 109.1 ?
C15 C14 H14B . . 109.1 ?
C13 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.9 ?
C14 C15 C16 . . 112.7(9) ?
C14 C15 H15A . . 109.1 ?
C16 C15 H15A . . 109.1 ?
C14 C15 H15B . . 109.1 ?
C16 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.8 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 C9 . 2.061(11) yes
Sn1 O1 . 2.075(5) yes
Sn1 O4 4_565 2.100(6) yes
Sn1 C13 . 2.117(9) yes
Sn1 O2 . 2.690(5) yes
F1 C3 . 1.337(9) ?
F2 C4 . 1.335(9) ?
F3 C5 . 1.343(9) ?
F4 C6 . 1.335(9) ?
O1 C1 . 1.308(9) yes
O2 C1 . 1.204(10) yes
O3 C8 . 1.219(10) yes
O4 C8 . 1.290(10) yes
O4 Sn1 4_566 2.100(6) yes
C1 C2 . 1.506(11) ?
C2 C3 . 1.369(11) ?
C2 C7 . 1.393(10) ?
C3 C4 . 1.377(12) ?
C4 C5 . 1.365(12) ?
C5 C6 . 1.352(11) ?
C6 C7 . 1.370(10) ?
C7 C8 . 1.510(11) ?
C9 C10 . 1.589(13) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.506(14) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.553(15) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.541(11) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.470(11) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.543(12) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
