#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/98/2219866.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_2219866
loop_
_publ_author_name
'Amini, Mostafa M.'
'Hajiashrafi, Taraneh'
'Kharat, Ali Nemati'
'Ng, Seik Weng'
_publ_section_title
;
 rac-(3-Hydroxy-2-phenylpropionato-κO)triphenyltin(IV)
;
_journal_coeditor_code           HB2813
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1403
_journal_paper_doi               10.1107/S160053680803242X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Sn (C6 H5)3 (C9 H9 O3)]'
_chemical_formula_moiety         'C27 H24 O3 Sn'
_chemical_formula_sum            'C27 H24 O3 Sn'
_chemical_formula_weight         515.15
_chemical_name_systematic
;
rac-(3-Hydroxy-2-phenylpropionato-κO)triphenyltin(IV)
;
_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           SHELXL97
_cell_angle_alpha                90.0870(10)
_cell_angle_beta                 103.6640(10)
_cell_angle_gamma                112.7580(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3880(2)
_cell_length_b                   9.4899(2)
_cell_length_c                   14.3399(2)
_cell_measurement_reflns_used    9425
_cell_measurement_temperature    112(2)
_cell_measurement_theta_max      32.6
_cell_measurement_theta_min      2.3
_cell_volume                     1138.58(4)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      112(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33531
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.148
_exptl_absorpt_correction_T_max  0.717
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.352
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         6612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0188
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0304P)²+0.5255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0493
_refine_ls_wR_factor_ref         0.0536
_reflns_number_gt                6339
_reflns_number_total             6612
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2813.cif
_cod_data_source_block           I
_cod_database_code               2219866
_cod_database_fobs_code          2219866
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.588742(10) 0.636637(10) 0.826066(6) 0.02043(3) Uani d . 1
O O1 0.74512(13) 0.76508(12) 0.74695(7) 0.0268(2) Uani d . 1
O O2 0.52531(13) 0.67054(13) 0.62949(8) 0.0303(2) Uani d . 1
O O3 0.71606(16) 0.55344(13) 0.51412(10) 0.0394(3) Uani d . 1
H H3 0.6449 0.4826 0.4734 0.059 Uiso calc R 1
C C1 0.54423(16) 0.40565(15) 0.78448(9) 0.0222(2) Uani d . 1
C C2 0.4203(2) 0.28743(18) 0.81068(12) 0.0330(3) Uani d . 1
H H2 0.3515 0.3111 0.8411 0.040 Uiso calc R 1
C C3 0.3973(3) 0.1349(2) 0.79226(15) 0.0441(4) Uani d . 1
H H3A 0.3129 0.0549 0.8102 0.053 Uiso calc R 1
C C4 0.4965(2) 0.09935(19) 0.74803(13) 0.0400(4) Uani d . 1
H H4 0.4812 -0.0048 0.7365 0.048 Uiso calc R 1
C C5 0.6186(2) 0.21545(19) 0.72034(12) 0.0334(3) Uani d . 1
H H5 0.6856 0.1908 0.6888 0.040 Uiso calc R 1
C C6 0.64278(18) 0.36822(17) 0.73878(11) 0.0274(3) Uani d . 1
H H6 0.7269 0.4476 0.7201 0.033 Uiso calc R 1
C C7 0.38486(17) 0.68487(16) 0.82227(12) 0.0275(3) Uani d . 1
C C8 0.25851(18) 0.64580(18) 0.73831(13) 0.0333(3) Uani d . 1
H H8 0.2686 0.6072 0.6802 0.040 Uiso calc R 1
C C9 0.1186(2) 0.6635(2) 0.74001(16) 0.0425(4) Uani d . 1
H H9 0.0335 0.6372 0.6831 0.051 Uiso calc R 1
C C10 0.1040(2) 0.7191(2) 0.82417(19) 0.0480(5) Uani d . 1
H H10 0.0082 0.7305 0.8252 0.058 Uiso calc R 1
C C11 0.2273(2) 0.7587(2) 0.90783(18) 0.0458(4) Uani d . 1
H H11 0.2160 0.7978 0.9655 0.055 Uiso calc R 1
C C12 0.3687(2) 0.74112(19) 0.90717(14) 0.0358(3) Uani d . 1
H H12 0.4531 0.7675 0.9644 0.043 Uiso calc R 1
C C13 0.76077(16) 0.71155(16) 0.96187(10) 0.0231(2) Uani d . 1
C C14 0.8361(2) 0.61586(19) 1.00105(11) 0.0323(3) Uani d . 1
H H14 0.8035 0.5161 0.9696 0.039 Uiso calc R 1
C C15 0.9590(2) 0.6657(2) 1.08601(13) 0.0427(4) Uani d . 1
H H15 1.0100 0.6001 1.1120 0.051 Uiso calc R 1
C C16 1.0063(2) 0.8105(2) 1.13220(12) 0.0407(4) Uani d . 1
H H16 1.0911 0.8451 1.1894 0.049 Uiso calc R 1
C C17 0.9304(2) 0.9052(2) 1.09543(12) 0.0366(3) Uani d . 1
H H17 0.9617 1.0038 1.1282 0.044 Uiso calc R 1
C C18 0.80848(19) 0.85653(17) 1.01073(11) 0.0296(3) Uani d . 1
H H18 0.7571 0.9223 0.9858 0.036 Uiso calc R 1
C C19 0.67104(17) 0.73973(16) 0.65568(10) 0.0242(2) Uani d . 1
C C20 0.77747(17) 0.80071(16) 0.58653(10) 0.0240(2) Uani d . 1
H H20 0.8833 0.7969 0.6167 0.029 Uiso calc R 1
C C21 0.7052(2) 0.69608(18) 0.49250(11) 0.0310(3) Uani d . 1
H H21A 0.5922 0.6808 0.4664 0.037 Uiso calc R 1
H H21B 0.7649 0.7415 0.4441 0.037 Uiso calc R 1
C C22 0.80597(18) 0.96785(16) 0.57297(10) 0.0248(3) Uani d . 1
C C23 0.6983(2) 1.0097(2) 0.50719(13) 0.0394(4) Uani d . 1
H H23 0.6010 0.9326 0.4703 0.047 Uiso calc R 1
C C24 0.7320(3) 1.1637(2) 0.49495(15) 0.0481(5) Uani d . 1
H H24 0.6583 1.1908 0.4490 0.058 Uiso calc R 1
C C25 0.8706(3) 1.2768(2) 0.54866(16) 0.0439(4) Uani d . 1
H H25 0.8932 1.3818 0.5399 0.053 Uiso calc R 1
C C26 0.9769(2) 1.2367(2) 0.61539(17) 0.0444(4) Uani d . 1
H H26 1.0719 1.3146 0.6538 0.053 Uiso calc R 1
C C27 0.9458(2) 1.08338(19) 0.62678(13) 0.0348(3) Uani d . 1
H H27 1.0212 1.0571 0.6719 0.042 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 Sn1 C1 104.08(5) n
O1 Sn1 C7 117.51(5) n
O1 Sn1 C13 94.95(5) n
C1 Sn1 C7 116.29(5) n
C1 Sn1 C13 109.17(5) n
C7 Sn1 C13 112.54(6) n
C19 O1 Sn1 109.50(9) ?
C21 O3 H3 109.5 ?
C6 C1 C2 118.99(13) ?
C6 C1 Sn1 122.04(10) ?
C2 C1 Sn1 118.77(11) ?
C3 C2 C1 120.14(15) ?
C3 C2 H2 119.9 ?
C1 C2 H2 119.9 ?
C4 C3 C2 120.38(16) ?
C4 C3 H3A 119.8 ?
C2 C3 H3A 119.8 ?
C3 C4 C5 120.09(15) ?
C3 C4 H4 120.0 ?
C5 C4 H4 120.0 ?
C6 C5 C4 119.92(15) ?
C6 C5 H5 120.0 ?
C4 C5 H5 120.0 ?
C5 C6 C1 120.48(14) ?
C5 C6 H6 119.8 ?
C1 C6 H6 119.8 ?
C12 C7 C8 119.39(15) ?
C12 C7 Sn1 119.13(12) ?
C8 C7 Sn1 121.13(12) ?
C9 C8 C7 120.32(17) ?
C9 C8 H8 119.8 ?
C7 C8 H8 119.8 ?
C10 C9 C8 119.76(18) ?
C10 C9 H9 120.1 ?
C8 C9 H9 120.1 ?
C11 C10 C9 120.90(17) ?
C11 C10 H10 119.5 ?
C9 C10 H10 119.5 ?
C10 C11 C12 119.91(19) ?
C10 C11 H11 120.0 ?
C12 C11 H11 120.0 ?
C7 C12 C11 119.71(18) ?
C7 C12 H12 120.1 ?
C11 C12 H12 120.1 ?
C18 C13 C14 118.58(14) ?
C18 C13 Sn1 122.64(11) ?
C14 C13 Sn1 118.67(11) ?
C15 C14 C13 120.55(16) ?
C15 C14 H14 119.7 ?
C13 C14 H14 119.7 ?
C16 C15 C14 119.92(17) ?
C16 C15 H15 120.0 ?
C14 C15 H15 120.0 ?
C15 C16 C17 120.18(16) ?
C15 C16 H16 119.9 ?
C17 C16 H16 119.9 ?
C18 C17 C16 120.14(16) ?
C18 C17 H17 119.9 ?
C16 C17 H17 119.9 ?
C17 C18 C13 120.60(15) ?
C17 C18 H18 119.7 ?
C13 C18 H18 119.7 ?
O2 C19 O1 120.51(13) ?
O2 C19 C20 123.92(13) ?
O1 C19 C20 115.57(12) ?
C22 C20 C21 113.37(12) ?
C22 C20 C19 110.50(11) ?
C21 C20 C19 109.60(12) ?
C22 C20 H20 107.7 ?
C21 C20 H20 107.7 ?
C19 C20 H20 107.7 ?
O3 C21 C20 106.66(13) ?
O3 C21 H21A 110.4 ?
C20 C21 H21A 110.4 ?
O3 C21 H21B 110.4 ?
C20 C21 H21B 110.4 ?
H21A C21 H21B 108.6 ?
C23 C22 C27 118.32(14) ?
C23 C22 C20 122.50(14) ?
C27 C22 C20 119.17(14) ?
C22 C23 C24 120.45(17) ?
C22 C23 H23 119.8 ?
C24 C23 H23 119.8 ?
C25 C24 C23 120.65(18) ?
C25 C24 H24 119.7 ?
C23 C24 H24 119.7 ?
C24 C25 C26 119.37(16) ?
C24 C25 H25 120.3 ?
C26 C25 H25 120.3 ?
C25 C26 C27 120.40(18) ?
C25 C26 H26 119.8 ?
C27 C26 H26 119.8 ?
C26 C27 C22 120.79(17) ?
C26 C27 H27 119.6 ?
C22 C27 H27 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Sn1 O1 2.0820(10) yes
Sn1 C1 2.1230(10) yes
Sn1 C7 2.1220(10) yes
Sn1 C13 2.1280(10) yes
O1 C19 1.3016(17) ?
O2 C19 1.2269(18) ?
O3 C21 1.4254(19) ?
O3 H3 0.8400 ?
C1 C6 1.397(2) ?
C1 C2 1.3970(19) ?
C2 C3 1.394(2) ?
C2 H2 0.9500 ?
C3 C4 1.380(3) ?
C3 H3A 0.9500 ?
C4 C5 1.387(3) ?
C4 H4 0.9500 ?
C5 C6 1.392(2) ?
C5 H5 0.9500 ?
C6 H6 0.9500 ?
C7 C12 1.392(2) ?
C7 C8 1.406(2) ?
C8 C9 1.393(2) ?
C8 H8 0.9500 ?
C9 C10 1.373(3) ?
C9 H9 0.9500 ?
C10 C11 1.388(3) ?
C10 H10 0.9500 ?
C11 C12 1.402(2) ?
C11 H11 0.9500 ?
C12 H12 0.9500 ?
C13 C18 1.399(2) ?
C13 C14 1.397(2) ?
C14 C15 1.397(2) ?
C14 H14 0.9500 ?
C15 C16 1.383(3) ?
C15 H15 0.9500 ?
C16 C17 1.383(3) ?
C16 H16 0.9500 ?
C17 C18 1.390(2) ?
C17 H17 0.9500 ?
C18 H18 0.9500 ?
C19 C20 1.5294(19) ?
C20 C22 1.5240(19) ?
C20 C21 1.519(2) ?
C20 H20 1.0000 ?
C21 H21A 0.9900 ?
C21 H21B 0.9900 ?
C22 C23 1.389(2) ?
C22 C27 1.388(2) ?
C23 C24 1.392(2) ?
C23 H23 0.9500 ?
C24 C25 1.372(3) ?
C24 H24 0.9500 ?
C25 C26 1.378(3) ?
C25 H25 0.9500 ?
C26 C27 1.387(2) ?
C26 H26 0.9500 ?
C27 H27 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 O2 2_666 0.84 1.98 2.819(2) 175 y
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
C1 Sn1 O1 C19 67.61(10)
C7 Sn1 O1 C19 -62.58(11)
C13 Sn1 O1 C19 178.80(10)
O1 Sn1 C1 C6 17.13(12)
C7 Sn1 C1 C6 148.04(11)
C13 Sn1 C1 C6 -83.32(12)
O1 Sn1 C1 C2 -168.17(11)
C7 Sn1 C1 C2 -37.26(13)
C13 Sn1 C1 C2 91.39(12)
C6 C1 C2 C3 0.7(2)
Sn1 C1 C2 C3 -174.13(14)
C1 C2 C3 C4 0.0(3)
C2 C3 C4 C5 -0.9(3)
C3 C4 C5 C6 1.1(3)
C4 C5 C6 C1 -0.4(2)
C2 C1 C6 C5 -0.5(2)
Sn1 C1 C6 C5 174.18(11)
O1 Sn1 C7 C12 -116.37(12)
C1 Sn1 C7 C12 119.36(12)
C13 Sn1 C7 C12 -7.63(14)
O1 Sn1 C7 C8 70.48(13)
C1 Sn1 C7 C8 -53.78(13)
C13 Sn1 C7 C8 179.23(11)
C12 C7 C8 C9 0.1(2)
Sn1 C7 C8 C9 173.25(12)
C7 C8 C9 C10 -0.1(3)
C8 C9 C10 C11 0.3(3)
C9 C10 C11 C12 -0.5(3)
C8 C7 C12 C11 -0.3(2)
Sn1 C7 C12 C11 -173.55(13)
C10 C11 C12 C7 0.5(3)
O1 Sn1 C13 C18 76.74(12)
C1 Sn1 C13 C18 -176.49(11)
C7 Sn1 C13 C18 -45.80(13)
O1 Sn1 C13 C14 -99.31(12)
C1 Sn1 C13 C14 7.46(13)
C7 Sn1 C13 C14 138.15(12)
C18 C13 C14 C15 -1.5(2)
Sn1 C13 C14 C15 174.73(14)
C13 C14 C15 C16 0.3(3)
C14 C15 C16 C17 1.1(3)
C15 C16 C17 C18 -1.4(3)
C16 C17 C18 C13 0.2(2)
C14 C13 C18 C17 1.2(2)
Sn1 C13 C18 C17 -174.81(12)
Sn1 O1 C19 O2 11.24(16)
Sn1 O1 C19 C20 -168.49(9)
O2 C19 C20 C22 93.95(17)
O1 C19 C20 C22 -86.33(15)
O2 C19 C20 C21 -31.69(19)
O1 C19 C20 C21 148.03(13)
C22 C20 C21 O3 168.43(12)
C19 C20 C21 O3 -67.59(15)
C21 C20 C22 C23 39.8(2)
C19 C20 C22 C23 -83.70(18)
C21 C20 C22 C27 -138.98(15)
C19 C20 C22 C27 97.53(16)
C27 C22 C23 C24 1.0(3)
C20 C22 C23 C24 -177.80(17)
C22 C23 C24 C25 -1.1(3)
C23 C24 C25 C26 -0.1(3)
C24 C25 C26 C27 1.4(3)
C25 C26 C27 C22 -1.5(3)
C23 C22 C27 C26 0.3(3)
C20 C22 C27 C26 179.09(15)
