#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:15:41 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178620 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/31/4073112.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_4073112
loop_
_publ_author_name
'Elhamzaoui, Hicham'
'Jousseaume, Bernard'
'Toupance, Thierry'
'Allouchi, Hassan'
_publ_section_title
;
 α,ω-Bis(trialkynyltin) Compounds with a Linear or Cross-Shaped Spacer
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              3908
_journal_paper_doi               10.1021/om070078p
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C20 H31 O Sn'
_chemical_formula_weight         406.14
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2007-01-15 # Formatted by publCIF
;
_cell_angle_alpha                110.247(4)
_cell_angle_beta                 102.111(4)
_cell_angle_gamma                89.552(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7368(3)
_cell_length_b                   10.8683(5)
_cell_length_c                   12.8803(6)
_cell_measurement_temperature    170(2)
_cell_volume                     991.03(8)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson,1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Xcalibure CCD'
_diffrn_measurement_method       φ
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20947
_diffrn_reflns_theta_full        33.09
_diffrn_reflns_theta_max         33.09
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    1.290
_exptl_absorpt_correction_T_max  0.8818
_exptl_absorpt_correction_T_min  0.6468
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'scale3 pack'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.146
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         6873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          6.994
_refine_ls_shift/su_mean         0.035
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0714
_reflns_number_gt                5093
_reflns_number_total             6873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om070078p-file001.cif
_cod_data_source_block           6MediC8terPh_7
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4073112
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Sn1 Sn 0.673108(17) 0.697691(13) 0.460274(10) 0.03167(5) Uani 1 1 d .
O2 O 0.69463(16) 0.63279(14) 0.98544(11) 0.0310(3) Uani 1 1 d .
C3 C 0.9346(2) 0.53978(16) 0.90568(14) 0.0225(3) Uani 1 1 d .
C4 C 1.0879(2) 0.47037(17) 0.91312(14) 0.0242(3) Uani 1 1 d .
H4 H 1.1493 0.4495 0.8532 0.029 Uiso 1 1 calc R
C5 C 0.8718(2) 0.57713(17) 0.80412(14) 0.0223(3) Uani 1 1 d .
C6 C 0.8471(2) 0.56872(16) 0.99520(14) 0.0234(3) Uani 1 1 d .
C7 C 0.7593(2) 0.73352(17) 0.71589(15) 0.0271(4) Uani 1 1 d .
H7 H 0.7187 0.8183 0.7238 0.033 Uiso 1 1 calc R
C8 C 0.8803(2) 0.48964(18) 0.69717(15) 0.0295(4) Uani 1 1 d .
H8 H 0.9225 0.4054 0.6896 0.035 Uiso 1 1 calc R
C9 C 0.6066(2) 0.66910(18) 1.07808(15) 0.0276(4) Uani 1 1 d .
H9A H 0.6882 0.7248 1.1490 0.033 Uiso 1 1 calc R
H9B H 0.5651 0.5898 1.0895 0.033 Uiso 1 1 calc R
C10 C 0.8099(2) 0.69997(17) 0.81172(15) 0.0260(3) Uani 1 1 d .
H10 H 0.8024 0.7616 0.8836 0.031 Uiso 1 1 calc R
C11 C 0.1875(2) 0.86444(19) 1.10598(16) 0.0307(4) Uani 1 1 d .
H11A H 0.2336 0.9421 1.0941 0.037 Uiso 1 1 calc R
H11B H 0.1125 0.8076 1.0328 0.037 Uiso 1 1 calc R
C12 C 0.8279(3) 0.52362(19) 0.60103(15) 0.0319(4) Uani 1 1 d .
H12 H 0.8343 0.4618 0.5290 0.038 Uiso 1 1 calc R
C13 C 0.4510(2) 0.74438(19) 1.04706(16) 0.0291(4) Uani 1 1 d .
H13A H 0.3730 0.6879 0.9749 0.035 Uiso 1 1 calc R
H13B H 0.4952 0.8224 1.0348 0.035 Uiso 1 1 calc R
C14 C 0.7660(2) 0.64680(18) 0.60848(15) 0.0275(4) Uani 1 1 d .
C15 C 0.0723(2) 0.91055(19) 1.19239(17) 0.0317(4) Uani 1 1 d .
H15A H 0.1459 0.9685 1.2657 0.038 Uiso 1 1 calc R
H15B H 0.0251 0.8334 1.2045 0.038 Uiso 1 1 calc R
C16 C -0.0818(2) 0.98491(19) 1.15450(16) 0.0308(4) Uani 1 1 d .
H16A H -0.0354 1.0519 1.1294 0.037 Uiso 1 1 calc R
H16B H -0.1651 0.9224 1.0882 0.037 Uiso 1 1 calc R
C17 C 0.3433(2) 0.78909(19) 1.13863(16) 0.0302(4) Uani 1 1 d .
H17A H 0.2988 0.7112 1.1509 0.036 Uiso 1 1 calc R
H17B H 0.4210 0.8459 1.2108 0.036 Uiso 1 1 calc R
C18 C -0.1835(3) 1.0525(2) 1.24490(19) 0.0424(5) Uani 1 1 d .
H18A H -0.0996 1.1104 1.3136 0.051 Uiso 1 1 calc R
H18B H -0.2392 0.9852 1.2656 0.051 Uiso 1 1 calc R
C19 C -0.3260(3) 1.1338(3) 1.2062(2) 0.0583(7) Uani 1 1 d .
H19A H -0.3896 1.1737 1.2667 0.087 Uiso 1 1 calc R
H19B H -0.4093 1.0770 1.1381 0.087 Uiso 1 1 calc R
H19C H -0.2710 1.2031 1.1888 0.087 Uiso 1 1 calc R
C20 C 0.6180(3) 0.5186(2) 0.31849(17) 0.0405(5) Uani 1 1 d .
H20A H 0.5753 0.5380 0.2489 0.061 Uiso 1 1 calc R
H20B H 0.5269 0.4638 0.3281 0.061 Uiso 1 1 calc R
H20C H 0.7263 0.4717 0.3132 0.061 Uiso 1 1 calc R
C21 C 0.4445(3) 0.8070(3) 0.4836(2) 0.0517(6) Uani 1 1 d .
H21A H 0.3995 0.8317 0.4171 0.078 Uiso 1 1 calc R
H21B H 0.4767 0.8866 0.5513 0.078 Uiso 1 1 calc R
H21C H 0.3526 0.7529 0.4932 0.078 Uiso 1 1 calc R
C22 C 0.8705(3) 0.8220(2) 0.44288(19) 0.0464(5) Uani 1 1 d .
H22A H 0.8267 0.8445 0.3751 0.070 Uiso 1 1 calc R
H22B H 0.9790 0.7757 0.4356 0.070 Uiso 1 1 calc R
H22C H 0.8961 0.9026 0.5100 0.070 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'
Sn Sn -0.6537 1.4246 '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'
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
C20 Sn1 C21 113.05(9) . .
C20 Sn1 C22 110.94(9) . .
C21 Sn1 C22 107.73(10) . .
C20 Sn1 C14 107.08(8) . .
C21 Sn1 C14 107.80(8) . .
C22 Sn1 C14 110.19(8) . .
C6 O2 C9 118.19(13) . .
C6 C3 C4 117.42(15) . .
C6 C3 C5 123.32(15) . .
C4 C3 C5 119.25(15) . .
C6 C4 C3 122.31(15) 2_767 .
C6 C4 H4 118.8 2_767 .
C3 C4 H4 118.8 . .
C8 C5 C10 117.75(15) . .
C8 C5 C3 119.82(15) . .
C10 C5 C3 122.39(15) . .
O2 C6 C4 122.76(15) . 2_767
O2 C6 C3 116.94(14) . .
C4 C6 C3 120.27(15) 2_767 .
C10 C7 C14 121.95(16) . .
C10 C7 H7 119.0 . .
C14 C7 H7 119.0 . .
C5 C8 C12 121.07(17) . .
C5 C8 H8 119.5 . .
C12 C8 H8 119.5 . .
O2 C9 C13 106.59(14) . .
O2 C9 H9A 110.4 . .
C13 C9 H9A 110.4 . .
O2 C9 H9B 110.4 . .
C13 C9 H9B 110.4 . .
H9A C9 H9B 108.6 . .
C7 C10 C5 120.90(16) . .
C7 C10 H10 119.6 . .
C5 C10 H10 119.6 . .
C15 C11 C17 114.74(16) . .
C15 C11 H11A 108.6 . .
C17 C11 H11A 108.6 . .
C15 C11 H11B 108.6 . .
C17 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
C8 C12 C14 121.27(17) . .
C8 C12 H12 119.4 . .
C14 C12 H12 119.4 . .
C9 C13 C17 112.42(15) . .
C9 C13 H13A 109.1 . .
C17 C13 H13A 109.1 . .
C9 C13 H13B 109.1 . .
C17 C13 H13B 109.1 . .
H13A C13 H13B 107.9 . .
C7 C14 C12 117.06(16) . .
C7 C14 Sn1 121.09(13) . .
C12 C14 Sn1 121.79(13) . .
C11 C15 C16 112.19(16) . .
C11 C15 H15A 109.2 . .
C16 C15 H15A 109.2 . .
C11 C15 H15B 109.2 . .
C16 C15 H15B 109.2 . .
H15A C15 H15B 107.9 . .
C18 C16 C15 114.56(17) . .
C18 C16 H16A 108.6 . .
C15 C16 H16A 108.6 . .
C18 C16 H16B 108.6 . .
C15 C16 H16B 108.6 . .
H16A C16 H16B 107.6 . .
C11 C17 C13 111.69(16) . .
C11 C17 H17A 109.3 . .
C13 C17 H17A 109.3 . .
C11 C17 H17B 109.3 . .
C13 C17 H17B 109.3 . .
H17A C17 H17B 107.9 . .
C16 C18 C19 112.54(19) . .
C16 C18 H18A 109.1 . .
C19 C18 H18A 109.1 . .
C16 C18 H18B 109.1 . .
C19 C18 H18B 109.1 . .
H18A C18 H18B 107.8 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
Sn1 C20 H20A 109.5 . .
Sn1 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
Sn1 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
Sn1 C21 H21A 109.5 . .
Sn1 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
Sn1 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
Sn1 C22 H22A 109.5 . .
Sn1 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
Sn1 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 C20 2.128(2) .
Sn1 C21 2.139(2) .
Sn1 C22 2.143(2) .
Sn1 C14 2.1483(17) .
O2 C6 1.3703(19) .
O2 C9 1.433(2) .
C3 C6 1.400(2) .
C3 C4 1.405(2) .
C3 C5 1.487(2) .
C4 C6 1.386(2) 2_767
C4 H4 0.9500 .
C5 C8 1.392(2) .
C5 C10 1.393(2) .
C6 C4 1.386(2) 2_767
C7 C10 1.384(2) .
C7 C14 1.390(3) .
C7 H7 0.9500 .
C8 C12 1.392(3) .
C8 H8 0.9500 .
C9 C13 1.512(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10 0.9500 .
C11 C15 1.519(3) .
C11 C17 1.520(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C14 1.397(3) .
C12 H12 0.9500 .
C13 C17 1.527(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C15 C16 1.526(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C18 1.516(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.517(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
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_4
C6 C3 C4 C6 -0.1(3) 2_767
C5 C3 C4 C6 -179.34(16) 2_767
C6 C3 C5 C8 -139.67(18) .
C4 C3 C5 C8 39.5(2) .
C6 C3 C5 C10 42.9(3) .
C4 C3 C5 C10 -138.00(18) .
C9 O2 C6 C4 4.7(2) 2_767
C9 O2 C6 C3 -177.18(16) .
C4 C3 C6 O2 -178.01(15) .
C5 C3 C6 O2 1.1(2) .
C4 C3 C6 C4 0.1(3) 2_767
C5 C3 C6 C4 179.30(16) 2_767
C10 C5 C8 C12 -0.3(3) .
C3 C5 C8 C12 -177.88(17) .
C6 O2 C9 C13 176.68(15) .
C14 C7 C10 C5 0.6(3) .
C8 C5 C10 C7 -0.2(3) .
C3 C5 C10 C7 177.33(16) .
C5 C8 C12 C14 0.4(3) .
O2 C9 C13 C17 179.68(16) .
C10 C7 C14 C12 -0.5(3) .
C10 C7 C14 Sn1 176.60(13) .
C8 C12 C14 C7 0.0(3) .
C8 C12 C14 Sn1 -177.08(14) .
C20 Sn1 C14 C7 -158.98(15) .
C21 Sn1 C14 C7 -37.06(17) .
C22 Sn1 C14 C7 80.26(16) .
C20 Sn1 C14 C12 17.97(17) .
C21 Sn1 C14 C12 139.90(16) .
C22 Sn1 C14 C12 -102.79(17) .
C17 C11 C15 C16 -179.77(16) .
C11 C15 C16 C18 -170.42(18) .
C15 C11 C17 C13 179.17(17) .
C9 C13 C17 C11 -179.95(16) .
C15 C16 C18 C19 175.5(2) .
