#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:22:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178622 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/33/4073397.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4073397
loop_
_publ_author_name
'Reeske, Gregor'
'Schürmann, Markus'
'Costisella, Burkhard'
'Jurkschat, Klaus'
_publ_section_title
;
 Ph(3-n)XnSnCH2-16-crown-5 (X = F, Cl, Br, I, SCN;n= 1, 2): 
 Intramolecular O → Sn Coordination versus Ditopic Complexation
 of Sodium Thiocyanate†
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4170
_journal_paper_doi               10.1021/om700304p
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C18 H28 I2 O5 Sn'
_chemical_formula_weight         696.89
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 98.525(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6467(2)
_cell_length_b                   13.5974(3)
_cell_length_c                   9.8469(2)
_cell_measurement_reflns_used    9504
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.93
_cell_volume                     1144.93(4)
_computing_cell_refinement
;
DENZO & SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO & SCALEPACK
;
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material
;
SHELXL97
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean '19 vertical, 18 horizontal'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method
;
 3 sets at different κ-angles and 263 frames via ω-rotation 
(Δ/ω=1°) at two times 20s per frame
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9504
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    3.835
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.972
_refine_diff_density_min         -1.156
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0211P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0581
_reflns_number_gt                1972
_reflns_number_total             2702
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700304p-file003.cif
_cod_data_source_block           compound8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               4073397
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.29336(3) 0.09630(2) 0.47379(2) 0.04463(10) Uani 1 1 d .
Sn1 Sn 0.10576(4) 0.2500 0.35159(3) 0.02831(11) Uani 1 2 d S
O1 O -0.1067(3) 0.14028(17) 0.2431(2) 0.0305(5) Uani 1 1 d .
O2 O -0.2030(3) 0.08487(18) -0.0354(2) 0.0379(6) Uani 1 1 d .
O3 O -0.3388(4) 0.2500 -0.1705(3) 0.0402(9) Uani 1 2 d S
C1 C 0.1773(5) 0.2500 0.1530(4) 0.0231(10) Uani 1 2 d S
C2 C 0.0728(5) 0.2500 0.0320(4) 0.0218(10) Uani 1 2 d S
H2A H -0.0343 0.2500 0.0347 0.026 Uiso 1 2 calc SR
C3 C 0.1280(6) 0.2500 -0.0928(4) 0.0246(11) Uani 1 2 d S
H3A H 0.0574 0.2500 -0.1739 0.030 Uiso 1 2 calc SR
C4 C 0.2867(6) 0.2500 -0.0987(4) 0.0284(11) Uani 1 2 d S
H4A H 0.3225 0.2500 -0.1832 0.034 Uiso 1 2 calc SR
C5 C 0.3923(6) 0.2500 0.0219(4) 0.0306(12) Uani 1 2 d S
H5A H 0.4994 0.2500 0.0192 0.037 Uiso 1 2 calc SR
C6 C 0.3358(5) 0.2500 0.1472(4) 0.0289(11) Uani 1 2 d S
H6A H 0.4062 0.2500 0.2284 0.035 Uiso 1 2 calc SR
C11 C -0.0732(6) 0.2500 0.4776(5) 0.0541(18) Uani 1 2 d S
H11A H -0.0640 0.1921 0.5359 0.065 Uiso 0.50 1 calc PR
H11B H -0.0640 0.3079 0.5359 0.065 Uiso 0.50 1 calc PR
C12 C -0.2309(6) 0.2500 0.3848(5) 0.0386(13) Uani 1 2 d S
H12 H -0.3124 0.2500 0.4441 0.046 Uiso 1 2 calc SR
C13 C -0.2494(4) 0.1563(3) 0.3001(4) 0.0372(9) Uani 1 1 d .
H13A H -0.2691 0.1011 0.3575 0.045 Uiso 1 1 calc R
H13B H -0.3372 0.1625 0.2268 0.045 Uiso 1 1 calc R
C14 C -0.0904(5) 0.0433(3) 0.1903(4) 0.0417(10) Uani 1 1 d .
H14A H -0.0953 -0.0039 0.2634 0.050 Uiso 1 1 calc R
H14B H 0.0118 0.0376 0.1617 0.050 Uiso 1 1 calc R
C17 C -0.3139(5) 0.1623(3) -0.2404(3) 0.0462(11) Uani 1 1 d .
H17A H -0.2106 0.1627 -0.2677 0.055 Uiso 1 1 calc R
H17B H -0.3909 0.1560 -0.3223 0.055 Uiso 1 1 calc R
C15 C -0.2124(5) 0.0178(3) 0.0717(4) 0.0464(10) Uani 1 1 d .
H15A H -0.1956 -0.0486 0.0408 0.056 Uiso 1 1 calc R
H15B H -0.3153 0.0208 0.0994 0.056 Uiso 1 1 calc R
C16 C -0.3283(5) 0.0789(3) -0.1450(4) 0.0453(10) Uani 1 1 d .
H16A H -0.4273 0.0827 -0.1101 0.054 Uiso 1 1 calc R
H16B H -0.3243 0.0168 -0.1930 0.054 Uiso 1 1 calc R
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'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 Sn1 C1 150.49(18) . .
C11 Sn1 O1 72.20(12) . .
C1 Sn1 O1 84.40(11) . .
C11 Sn1 O1 72.20(12) . 4_565
C1 Sn1 O1 84.40(11) . 4_565
O1 Sn1 O1 73.90(10) . 4_565
C11 Sn1 I1 100.05(9) . 4_565
C1 Sn1 I1 99.51(8) . 4_565
O1 Sn1 I1 167.57(5) . 4_565
O1 Sn1 I1 94.63(5) 4_565 4_565
C11 Sn1 I1 100.05(9) . .
C1 Sn1 I1 99.51(8) . .
O1 Sn1 I1 94.63(5) . .
O1 Sn1 I1 167.57(5) 4_565 .
I1 Sn1 I1 96.327(14) 4_565 .
C14 O1 C13 114.5(3) . .
C14 O1 Sn1 127.1(2) . .
C13 O1 Sn1 111.26(19) . .
C15 O2 C16 114.4(3) . .
C17 O3 C17 115.6(4) . 4_565
C6 C1 C2 119.3(4) . .
C6 C1 Sn1 117.5(3) . .
C2 C1 Sn1 123.2(3) . .
C3 C2 C1 119.8(4) . .
C4 C3 C2 120.9(4) . .
C3 C4 C5 119.7(4) . .
C4 C5 C6 119.1(5) . .
C1 C6 C5 121.2(4) . .
C12 C11 Sn1 108.3(3) . .
C13 C12 C13 114.1(4) . 4_565
C13 C12 C11 110.0(3) . .
C13 C12 C11 110.0(3) 4_565 .
O1 C13 C12 108.2(3) . .
O1 C14 C15 113.7(3) . .
O3 C17 C16 107.6(3) . .
O2 C15 C14 108.8(3) . .
O2 C16 C17 108.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Sn1 2.8050(3) .
Sn1 C11 2.123(5) .
Sn1 C1 2.137(4) .
Sn1 O1 2.482(2) .
Sn1 O1 2.482(2) 4_565
Sn1 I1 2.8050(3) 4_565
O1 C14 1.432(4) .
O1 C13 1.446(4) .
O2 C15 1.406(4) .
O2 C16 1.414(4) .
O3 C17 1.409(4) .
O3 C17 1.409(4) 4_565
C1 C6 1.380(6) .
C1 C2 1.384(6) .
C2 C3 1.383(6) .
C3 C4 1.382(7) .
C4 C5 1.387(6) .
C5 C6 1.392(6) .
C11 C12 1.525(7) .
C12 C13 1.518(4) .
C12 C13 1.518(4) 4_565
C14 C15 1.494(5) .
C17 C16 1.490(5) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C11 Sn1 O1 C14 -132.9(3) . .
C1 Sn1 O1 C14 65.3(2) . .
O1 Sn1 O1 C14 151.1(2) 4_565 .
I1 Sn1 O1 C14 174.39(19) 4_565 .
I1 Sn1 O1 C14 -33.8(2) . .
C11 Sn1 O1 C13 15.7(2) . .
C1 Sn1 O1 C13 -146.1(2) . .
O1 Sn1 O1 C13 -60.3(2) 4_565 .
I1 Sn1 O1 C13 -37.1(3) 4_565 .
I1 Sn1 O1 C13 114.76(18) . .
C11 Sn1 C1 C6 180.0 . .
O1 Sn1 C1 C6 -142.84(5) . .
O1 Sn1 C1 C6 142.84(5) 4_565 .
I1 Sn1 C1 C6 49.063(18) 4_565 .
I1 Sn1 C1 C6 -49.063(18) . .
C11 Sn1 C1 C2 0.0 . .
O1 Sn1 C1 C2 37.16(5) . .
O1 Sn1 C1 C2 -37.16(5) 4_565 .
I1 Sn1 C1 C2 -130.937(18) 4_565 .
I1 Sn1 C1 C2 130.937(18) . .
C6 C1 C2 C3 0.0 . .
Sn1 C1 C2 C3 180.0 . .
C1 C2 C3 C4 0.0 . .
C2 C3 C4 C5 0.0 . .
C3 C4 C5 C6 0.0 . .
C2 C1 C6 C5 0.0 . .
Sn1 C1 C6 C5 180.0 . .
C4 C5 C6 C1 0.0 . .
C1 Sn1 C11 C12 0.000(1) . .
O1 Sn1 C11 C12 -39.15(6) . .
O1 Sn1 C11 C12 39.15(6) 4_565 .
I1 Sn1 C11 C12 130.83(2) 4_565 .
I1 Sn1 C11 C12 -130.83(2) . .
Sn1 C11 C12 C13 63.3(3) . .
Sn1 C11 C12 C13 -63.3(3) . 4_565
C14 O1 C13 C12 164.9(3) . .
Sn1 O1 C13 C12 12.2(3) . .
C13 C12 C13 O1 77.5(5) 4_565 .
C11 C12 C13 O1 -46.7(4) . .
C13 O1 C14 C15 63.4(4) . .
Sn1 O1 C14 C15 -148.9(2) . .
C17 O3 C17 C16 173.8(3) 4_565 .
C16 O2 C15 C14 -170.1(3) . .
O1 C14 C15 O2 59.8(4) . .
C15 O2 C16 C17 172.5(3) . .
O3 C17 C16 O2 -66.5(4) . .
