#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:25:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178898 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/27/4112725.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_4112725
loop_
_publ_author_name
'Hicham Elhamzaoui'
'Bernard Jousseaume'
'Hocine Riague'
'Thierry Toupance'
'Philippe Dieudonné'
'Cécile Zakri'
'Maryse Maugey'
'Hassan Allouchi'
_publ_contact_author             'Dr. Bernard Jousseaume'
_publ_contact_author_email       b.jousseaume@lcoo.u-bordeaux1.fr
_publ_contact_author_fax         33(0)540006994
_publ_contact_author_phone       33(0)540006443
_publ_section_title
;
 Self-Assembled Tin-Based Bridged Hybrid Materials
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8130
_journal_page_last               8131
_journal_paper_doi               10.1021/ja048272f
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C25 H39 Sn'
_chemical_formula_weight         458.25
_chemical_name_systematic
;
 4,4'-bis(tricyclohexylstannylmethyl)biphenyl
;
_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_date             2004-03-19T13:51:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                96.19(2)
_cell_angle_beta                 102.92(1)
_cell_angle_gamma                110.07(2)
_cell_formula_units_Z            2
_cell_length_a                   8.548(2)
_cell_length_b                   10.347(4)
_cell_length_c                   14.667(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      10
_cell_volume                     1163.2(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf CAD-4'
_diffrn_measurement_method       ω-2t
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6950
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.8094
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   3
        Theta correction was applied.
        Averaged transmission function was used.
        No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       needle
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.568
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         6731
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0797
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0787P)²+4.5340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1838
_refine_ls_wR_factor_ref         0.2089
_reflns_number_gt                3533
_reflns_number_total             6731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja048272fsi20040524_034913.cif
_cod_data_source_block           H.Allouchi
_cod_database_code               4112725
#BEGIN Tags that were not found in dictionaries:
_exptl_absorpt_correction_t_ave  0.8837
_exptl_absorpt_rmerge_before     0.0149
_exptl_absorpt_rmerge_after      0.0149
_exptl_absorpt_theta_corr_max    1.0000
_exptl_absorpt_theta_corr_min    0.9992
#END Tags that were not found in dictionaries
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 0.01833(7) 0.30253(6) 0.26555(4) 0.04122(19) Uani 1 1 d .
C25 C -0.1255(12) 0.1522(11) 0.4915(7) 0.069(3) Uani 1 1 d D
H25 H -0.0149 0.1516 0.5133 0.083 Uiso 1 1 calc R
C20 C -0.1482(11) 0.2456(9) 0.4366(6) 0.051(2) Uani 1 1 d D
C1 C -0.1909(13) 0.3196(15) 0.1615(8) 0.094(4) Uani 1 1 d D
H1 H -0.2138 0.3956 0.1948 0.112 Uiso 1 1 calc R
C23 C -0.4269(10) 0.0502(8) 0.4869(5) 0.0430(17) Uani 1 1 d .
C7 C 0.2611(10) 0.4674(8) 0.2669(6) 0.0444(18) Uani 1 1 d .
H7 H 0.2726 0.4578 0.2018 0.053 Uiso 1 1 calc R
C24 C -0.2598(12) 0.0588(11) 0.5159(7) 0.068(3) Uani 1 1 d .
H24 H -0.2359 -0.002 0.5542 0.082 Uiso 1 1 calc R
C8 C 0.2651(12) 0.6134(9) 0.2962(7) 0.059(2) Uani 1 1 d .
H8A H 0.1719 0.6261 0.2513 0.071 Uiso 1 1 calc R
H8B H 0.2455 0.6232 0.3588 0.071 Uiso 1 1 calc R
C14 C -0.1144(14) -0.0268(10) 0.2317(9) 0.076(3) Uani 1 1 d .
H14A H -0.2055 -0.0293 0.1776 0.092 Uiso 1 1 calc R
H14B H -0.1539 -0.0202 0.2885 0.092 Uiso 1 1 calc R
C21 C -0.3185(13) 0.2356(12) 0.4035(7) 0.069(3) Uani 1 1 d .
H21 H -0.3413 0.2954 0.3641 0.083 Uiso 1 1 calc R
C19 C -0.0041(12) 0.3523(10) 0.4075(7) 0.063(2) Uani 1 1 d .
H19A H 0.1055 0.3672 0.4526 0.075 Uiso 1 1 calc R
H19B H -0.0202 0.4409 0.4141 0.075 Uiso 1 1 calc R
C9 C 0.4359(15) 0.7262(9) 0.2993(8) 0.074(3) Uani 1 1 d .
H9A H 0.4361 0.8175 0.3228 0.089 Uiso 1 1 calc R
H9B H 0.449 0.7243 0.2352 0.089 Uiso 1 1 calc R
C12 C 0.4138(12) 0.4484(10) 0.3309(8) 0.067(3) Uani 1 1 d .
H12A H 0.4135 0.3568 0.3079 0.08 Uiso 1 1 calc R
H12B H 0.4005 0.4507 0.395 0.08 Uiso 1 1 calc R
C22 C -0.4534(12) 0.1420(12) 0.4263(8) 0.069(3) Uani 1 1 d .
H22 H -0.565 0.1387 0.4013 0.083 Uiso 1 1 calc R
C4 C -0.4426(18) 0.288(2) -0.0197(10) 0.147(8) Uani 1 1 d D
H4A H -0.4378 0.2138 -0.0642 0.177 Uiso 1 1 calc R
H4B H -0.5303 0.319 -0.0532 0.177 Uiso 1 1 calc R
C13 C 0.0479(11) 0.1014(9) 0.2427(7) 0.053(2) Uani 1 1 d .
H13 H 0.1356 0.1021 0.2989 0.064 Uiso 1 1 calc R
C10 C 0.5883(13) 0.7051(11) 0.3637(9) 0.077(3) Uani 1 1 d .
H10A H 0.6959 0.7754 0.3609 0.093 Uiso 1 1 calc R
H10B H 0.5825 0.7182 0.4291 0.093 Uiso 1 1 calc R
C15 C -0.0800(18) -0.1621(11) 0.2165(9) 0.086(4) Uani 1 1 d .
H15A H 0.0035 -0.1634 0.273 0.104 Uiso 1 1 calc R
H15B H -0.1868 -0.2424 0.207 0.104 Uiso 1 1 calc R
C17 C 0.152(2) -0.0495(13) 0.1441(12) 0.109(5) Uani 1 1 d .
H17A H 0.1932 -0.0566 0.0881 0.131 Uiso 1 1 calc R
H17B H 0.2404 -0.0478 0.1991 0.131 Uiso 1 1 calc R
C18 C 0.1160(18) 0.0862(12) 0.1582(10) 0.088(4) Uani 1 1 d .
H18A H 0.2226 0.1663 0.1667 0.106 Uiso 1 1 calc R
H18B H 0.0324 0.086 0.1012 0.106 Uiso 1 1 calc R
C16 C -0.0118(16) -0.1734(11) 0.1318(9) 0.082(3) Uani 1 1 d .
H16A H -0.098 -0.1779 0.0746 0.098 Uiso 1 1 calc R
H16B H 0.0109 -0.259 0.1243 0.098 Uiso 1 1 calc R
C11 C 0.5885(13) 0.5616(13) 0.3348(11) 0.097(4) Uani 1 1 d .
H11A H 0.6809 0.5491 0.3804 0.117 Uiso 1 1 calc R
H11B H 0.6095 0.5523 0.2726 0.117 Uiso 1 1 calc R
C2 C -0.3629(15) 0.2006(18) 0.1314(11) 0.130(6) Uani 1 1 d D
H2A H -0.4029 0.1821 0.1873 0.156 Uiso 1 1 calc R
H2B H -0.3493 0.117 0.1036 0.156 Uiso 1 1 calc R
C6 C -0.1356(16) 0.3764(18) 0.0787(10) 0.123(6) Uani 1 1 d .
H6A H -0.1005 0.3101 0.045 0.148 Uiso 1 1 calc R
H6B H -0.035 0.4635 0.1035 0.148 Uiso 1 1 calc R
C3 C -0.4981(16) 0.228(2) 0.0600(11) 0.150(8) Uani 1 1 d D
H3A H -0.5973 0.1408 0.0336 0.181 Uiso 1 1 calc R
H3B H -0.5365 0.2924 0.0937 0.181 Uiso 1 1 calc R
C5 C -0.2762(19) 0.4047(17) 0.0068(11) 0.130(6) Uani 1 1 d D
H5A H -0.2891 0.4885 0.0347 0.156 Uiso 1 1 calc R
H5B H -0.2392 0.4219 -0.0502 0.156 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 0 '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
_geom_angle_site_symmetry_3
C1 Sn1 C19 110.2(5) .
C1 Sn1 C13 115.1(4) .
C19 Sn1 C13 110.5(4) .
C1 Sn1 C7 109.0(4) .
C19 Sn1 C7 103.3(3) .
C13 Sn1 C7 108.1(3) .
C20 C25 C24 122.3(9) .
C20 C25 H25 118.9 .
C24 C25 H25 118.9 .
C25 C20 C21 115.3(8) .
C25 C20 C19 124.8(9) .
C21 C20 C19 119.9(8) .
C2 C1 C6 112.8(11) .
C2 C1 Sn1 118.9(10) .
C6 C1 Sn1 112.6(8) .
C2 C1 H1 103.4 .
C6 C1 H1 103.4 .
Sn1 C1 H1 103.4 .
C24 C23 C22 114.8(8) .
C24 C23 C23 123.8(9) 2_456
C22 C23 C23 121.4(9) 2_456
C8 C7 C12 110.4(7) .
C8 C7 Sn1 112.8(6) .
C12 C7 Sn1 110.5(5) .
C8 C7 H7 107.6 .
C12 C7 H7 107.6 .
Sn1 C7 H7 107.6 .
C23 C24 C25 123.4(9) .
C23 C24 H24 118.3 .
C25 C24 H24 118.3 .
C9 C8 C7 112.1(8) .
C9 C8 H8A 109.2 .
C7 C8 H8A 109.2 .
C9 C8 H8B 109.2 .
C7 C8 H8B 109.2 .
H8A C8 H8B 107.9 .
C13 C14 C15 111.1(9) .
C13 C14 H14A 109.4 .
C15 C14 H14A 109.4 .
C13 C14 H14B 109.4 .
C15 C14 H14B 109.4 .
H14A C14 H14B 108 .
C22 C21 C20 122.9(9) .
C22 C21 H21 118.5 .
C20 C21 H21 118.5 .
C20 C19 Sn1 117.5(6) .
C20 C19 H19A 107.9 .
Sn1 C19 H19A 107.9 .
C20 C19 H19B 107.9 .
Sn1 C19 H19B 107.9 .
H19A C19 H19B 107.2 .
C8 C9 C10 111.4(8) .
C8 C9 H9A 109.4 .
C10 C9 H9A 109.4 .
C8 C9 H9B 109.4 .
C10 C9 H9B 109.4 .
H9A C9 H9B 108 .
C7 C12 C11 112.8(8) .
C7 C12 H12A 109 .
C11 C12 H12A 109 .
C7 C12 H12B 109 .
C11 C12 H12B 109 .
H12A C12 H12B 107.8 .
C21 C22 C23 121.2(9) .
C21 C22 H22 119.4 .
C23 C22 H22 119.4 .
C5 C4 C3 115.6(13) .
C5 C4 H4A 108.4 .
C3 C4 H4A 108.4 .
C5 C4 H4B 108.4 .
C3 C4 H4B 108.4 .
H4A C4 H4B 107.4 .
C18 C13 C14 109.3(8) .
C18 C13 Sn1 110.6(6) .
C14 C13 Sn1 115.2(6) .
C18 C13 H13 107.1 .
C14 C13 H13 107.1 .
Sn1 C13 H13 107.1 .
C11 C10 C9 111.9(9) .
C11 C10 H10A 109.2 .
C9 C10 H10A 109.2 .
C11 C10 H10B 109.2 .
C9 C10 H10B 109.2 .
H10A C10 H10B 107.9 .
C16 C15 C14 111.1(9) .
C16 C15 H15A 109.4 .
C14 C15 H15A 109.4 .
C16 C15 H15B 109.4 .
C14 C15 H15B 109.4 .
H15A C15 H15B 108 .
C16 C17 C18 109.4(11) .
C16 C17 H17A 109.8 .
C18 C17 H17A 109.8 .
C16 C17 H17B 109.8 .
C18 C17 H17B 109.8 .
H17A C17 H17B 108.2 .
C13 C18 C17 112.2(10) .
C13 C18 H18A 109.2 .
C17 C18 H18A 109.2 .
C13 C18 H18B 109.2 .
C17 C18 H18B 109.2 .
H18A C18 H18B 107.9 .
C15 C16 C17 110.4(10) .
C15 C16 H16A 109.6 .
C17 C16 H16A 109.6 .
C15 C16 H16B 109.6 .
C17 C16 H16B 109.6 .
H16A C16 H16B 108.1 .
C10 C11 C12 110.3(10) .
C10 C11 H11A 109.6 .
C12 C11 H11A 109.6 .
C10 C11 H11B 109.6 .
C12 C11 H11B 109.6 .
H11A C11 H11B 108.1 .
C1 C2 C3 113.1(13) .
C1 C2 H2A 109 .
C3 C2 H2A 109 .
C1 C2 H2B 109 .
C3 C2 H2B 109 .
H2A C2 H2B 107.8 .
C1 C6 C5 114.7(12) .
C1 C6 H6A 108.6 .
C5 C6 H6A 108.6 .
C1 C6 H6B 108.6 .
C5 C6 H6B 108.6 .
H6A C6 H6B 107.6 .
C4 C3 C2 115.8(13) .
C4 C3 H3A 108.3 .
C2 C3 H3A 108.3 .
C4 C3 H3B 108.3 .
C2 C3 H3B 108.3 .
H3A C3 H3B 107.4 .
C4 C5 C6 112.2(12) .
C4 C5 H5A 109.2 .
C6 C5 H5A 109.2 .
C4 C5 H5B 109.2 .
C6 C5 H5B 109.2 .
H5A C5 H5B 107.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 C1 2.147(12) .
Sn1 C19 2.156(9) .
Sn1 C13 2.180(9) .
Sn1 C7 2.182(7) .
C25 C20 1.360(11) .
C25 C24 1.370(13) .
C25 H25 0.93 .
C20 C21 1.391(13) .
C20 C19 1.525(11) .
C1 C2 1.491(13) .
C1 C6 1.505(17) .
C1 H1 0.98 .
C23 C24 1.365(12) .
C23 C22 1.409(12) .
C23 C23 1.483(15) 2_456
C7 C8 1.512(12) .
C7 C12 1.514(12) .
C7 H7 0.98 .
C24 H24 0.93 .
C8 C9 1.512(13) .
C8 H8A 0.97 .
C8 H8B 0.97 .
C14 C13 1.517(12) .
C14 C15 1.530(15) .
C14 H14A 0.97 .
C14 H14B 0.97 .
C21 C22 1.361(13) .
C21 H21 0.93 .
C19 H19A 0.97 .
C19 H19B 0.97 .
C9 C10 1.525(15) .
C9 H9A 0.97 .
C9 H9B 0.97 .
C12 C11 1.533(14) .
C12 H12A 0.97 .
C12 H12B 0.97 .
C22 H22 0.93 .
C4 C5 1.451(14) .
C4 C3 1.475(14) .
C4 H4A 0.97 .
C4 H4B 0.97 .
C13 C18 1.499(14) .
C13 H13 0.98 .
C10 C11 1.500(17) .
C10 H10A 0.97 .
C10 H10B 0.97 .
C15 C16 1.495(16) .
C15 H15A 0.97 .
C15 H15B 0.97 .
C17 C16 1.495(17) .
C17 C18 1.538(16) .
C17 H17A 0.97 .
C17 H17B 0.97 .
C18 H18A 0.97 .
C18 H18B 0.97 .
C16 H16A 0.97 .
C16 H16B 0.97 .
C11 H11A 0.97 .
C11 H11B 0.97 .
C2 C3 1.505(19) .
C2 H2A 0.97 .
C2 H2B 0.97 .
C6 C5 1.544(18) .
C6 H6A 0.97 .
C6 H6B 0.97 .
C3 H3A 0.97 .
C3 H3B 0.97 .
C5 H5A 0.97 .
C5 H5B 0.97 .
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
C24 C25 C20 C21 -2.7(15) .
C24 C25 C20 C19 179.7(10) .
C19 Sn1 C1 C2 -81.1(12) .
C13 Sn1 C1 C2 44.7(13) .
C7 Sn1 C1 C2 166.2(11) .
C19 Sn1 C1 C6 143.7(11) .
C13 Sn1 C1 C6 -90.5(12) .
C7 Sn1 C1 C6 31.0(12) .
C1 Sn1 C7 C8 62.5(7) .
C19 Sn1 C7 C8 -54.7(7) .
C13 Sn1 C7 C8 -171.8(6) .
C1 Sn1 C7 C12 -173.4(7) .
C19 Sn1 C7 C12 69.4(7) .
C13 Sn1 C7 C12 -47.7(7) .
C22 C23 C24 C25 2.3(16) .
C23 C23 C24 C25 -179.8(11) 2_456
C20 C25 C24 C23 0.6(18) .
C12 C7 C8 C9 54.3(10) .
Sn1 C7 C8 C9 178.4(7) .
C25 C20 C21 C22 1.8(16) .
C19 C20 C21 C22 179.6(10) .
C25 C20 C19 Sn1 100.5(10) .
C21 C20 C19 Sn1 -77.0(11) .
C1 Sn1 C19 C20 72.1(9) .
C13 Sn1 C19 C20 -56.2(8) .
C7 Sn1 C19 C20 -171.6(7) .
C7 C8 C9 C10 -54.9(12) .
C8 C7 C12 C11 -54.5(12) .
Sn1 C7 C12 C11 -179.9(8) .
C20 C21 C22 C23 1.1(18) .
C24 C23 C22 C21 -3.0(15) .
C23 C23 C22 C21 179.0(11) 2_456
C15 C14 C13 C18 55.0(13) .
C15 C14 C13 Sn1 -179.8(8) .
C1 Sn1 C13 C18 71.4(8) .
C19 Sn1 C13 C18 -163.0(7) .
C7 Sn1 C13 C18 -50.6(8) .
C1 Sn1 C13 C14 -53.2(9) .
C19 Sn1 C13 C14 72.4(8) .
C7 Sn1 C13 C14 -175.2(7) .
C8 C9 C10 C11 55.3(13) .
C13 C14 C15 C16 -56.7(14) .
C14 C13 C18 C17 -56.4(14) .
Sn1 C13 C18 C17 175.7(9) .
C16 C17 C18 C13 58.3(16) .
C14 C15 C16 C17 58.2(15) .
C18 C17 C16 C15 -58.0(16) .
C9 C10 C11 C12 -54.4(14) .
C7 C12 C11 C10 54.8(14) .
C6 C1 C2 C3 -46(2) .
Sn1 C1 C2 C3 178.6(12) .
C2 C1 C6 C5 48(2) .
Sn1 C1 C6 C5 -174.2(12) .
C5 C4 C3 C2 -47(3) .
C1 C2 C3 C4 46(2) .
C3 C4 C5 C6 46(3) .
C1 C6 C5 C4 -47(2) .
