#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/33/2213346.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_2213346
loop_
_publ_author_name
'Yang, Hong-Jun'
'Tian, Lai-Jin'
'Zhang, Chang-Fa'
'Zheng, Xiao-Feng'
_publ_section_title
'[N-(3,5-Dibromo-2-oxidobenzylidene)phenylalaninato-κ³O,N,O']diphenyltin(IV)'
_journal_coeditor_code           HB2356
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1272
_journal_page_last               m1273
_journal_paper_doi               10.1107/S1600536807015152
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Sn (C6 H5)2 (C16 H11 Br2 N O3)]'
_chemical_formula_moiety         'C28 H21 Br2 N O3 Sn'
_chemical_formula_sum            'C28 H21 Br2 N O3 Sn'
_chemical_formula_weight         697.97
_chemical_name_systematic
;
[N-(3,5-Dibromo-2-oxidophenylmethylene)phenylalaninato-
κ³O,N,O']diphenyltin(IV)
;
_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                 113.0740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2880(7)
_cell_length_b                   23.3977(15)
_cell_length_c                   10.7391(7)
_cell_measurement_reflns_used    8422
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.38
_cell_volume                     2609.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20999
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.072
_exptl_absorpt_correction_T_max  0.737
_exptl_absorpt_correction_T_min  0.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.436
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0310
_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)+(0.037P)²+1.2833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                4566
_reflns_number_total             5406
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2356.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213346
_cod_database_fobs_code          2213346
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 0.474431(18) 0.133619(9) 0.195341(19) 0.03985(8) Uani d . 1
Br Br2 1.12340(4) 0.074850(19) 0.73326(4) 0.07264(13) Uani d . 1
Br Br1 0.68270(4) 0.211054(19) 0.64691(4) 0.07253(13) Uani d . 1
N N1 0.6396(2) 0.10314(11) 0.1593(2) 0.0394(5) Uani d . 1
O O1 0.6174(2) 0.17443(9) 0.3594(2) 0.0484(5) Uani d . 1
O O2 0.39397(19) 0.08769(10) 0.0115(2) 0.0494(5) Uani d . 1
O O3 0.4269(2) 0.03756(10) -0.1470(2) 0.0557(6) Uani d . 1
C C1 0.7265(3) 0.15108(13) 0.4389(3) 0.0441(7) Uani d . 1
C C2 0.7791(3) 0.16368(14) 0.5787(3) 0.0499(7) Uani d . 1
C C3 0.8948(3) 0.14149(15) 0.6652(3) 0.0550(9) Uani d . 1
H H3 0.9271 0.1506 0.7568 0.066 Uiso calc R 1
C C4 0.9629(3) 0.10560(16) 0.6150(3) 0.0537(8) Uani d . 1
C C5 0.9167(3) 0.09150(15) 0.4800(3) 0.0511(8) Uani d . 1
H H5 0.9637 0.0675 0.4474 0.061 Uiso calc R 1
C C6 0.7973(3) 0.11376(14) 0.3914(3) 0.0429(7) Uani d . 1
C C7 0.7516(3) 0.09433(13) 0.2533(3) 0.0429(7) Uani d . 1
H H7 0.8092 0.0731 0.2294 0.051 Uiso calc R 1
C C8 0.6110(3) 0.07839(13) 0.0250(3) 0.0410(6) Uani d . 1
H H8 0.6581 0.0423 0.0362 0.049 Uiso calc R 1
C C9 0.4662(3) 0.06597(13) -0.0444(3) 0.0426(7) Uani d . 1
C C10 0.6515(3) 0.11819(15) -0.0644(3) 0.0501(8) Uani d . 1
H H10A 0.6215 0.1024 -0.1551 0.060 Uiso calc R 1
H H10B 0.6103 0.1550 -0.0701 0.060 Uiso calc R 1
C C11 0.7957(3) 0.12672(15) -0.0119(3) 0.0499(8) Uani d . 1
C C12 0.8785(4) 0.08146(19) 0.0116(4) 0.0720(11) Uani d . 1
H H12 0.8454 0.0446 -0.0071 0.086 Uiso calc R 1
C C13 1.0095(4) 0.0894(3) 0.0621(6) 0.0999(16) Uani d . 1
H H13 1.0642 0.0581 0.0779 0.120 Uiso calc R 1
C C14 1.0589(5) 0.1427(4) 0.0887(6) 0.118(2) Uani d . 1
H H14 1.1477 0.1480 0.1249 0.141 Uiso calc R 1
C C15 0.9795(6) 0.1886(3) 0.0630(6) 0.1069(19) Uani d . 1
H H15 1.0136 0.2254 0.0786 0.128 Uiso calc R 1
C C16 0.8480(4) 0.18060(19) 0.0135(4) 0.0727(11) Uani d . 1
H H16 0.7939 0.2122 -0.0029 0.087 Uiso calc R 1
C C17 0.3792(3) 0.21079(13) 0.1141(3) 0.0447(7) Uani d . 1
C C18 0.3923(4) 0.25718(17) 0.1965(4) 0.0668(10) Uani d . 1
H H18 0.4502 0.2556 0.2864 0.080 Uiso calc R 1
C C19 0.3205(5) 0.3062(2) 0.1480(5) 0.0861(13) Uani d . 1
H H19 0.3306 0.3374 0.2049 0.103 Uiso calc R 1
C C20 0.2353(5) 0.3086(2) 0.0173(6) 0.0900(15) Uani d . 1
H H20 0.1871 0.3416 -0.0153 0.108 Uiso calc R 1
C C21 0.2202(5) 0.2632(2) -0.0660(5) 0.0924(15) Uani d . 1
H H21 0.1612 0.2650 -0.1553 0.111 Uiso calc R 1
C C22 0.2926(4) 0.21415(18) -0.0183(4) 0.0712(11) Uani d . 1
H H22 0.2826 0.1833 -0.0761 0.085 Uiso calc R 1
C C23 0.4083(3) 0.07794(13) 0.3088(3) 0.0450(7) Uani d . 1
C C24 0.4279(4) 0.09094(17) 0.4403(4) 0.0639(9) Uani d . 1
H H24 0.4746 0.1234 0.4810 0.077 Uiso calc R 1
C C25 0.3783(4) 0.0560(2) 0.5125(4) 0.0778(12) Uani d . 1
H H25 0.3930 0.0646 0.6019 0.093 Uiso calc R 1
C C26 0.3084(5) 0.00912(19) 0.4526(5) 0.0803(13) Uani d . 1
H H26 0.2732 -0.0137 0.5003 0.096 Uiso calc R 1
C C27 0.2897(5) -0.0046(2) 0.3233(5) 0.0921(15) Uani d . 1
H H27 0.2435 -0.0373 0.2834 0.111 Uiso calc R 1
C C28 0.3392(4) 0.02979(16) 0.2516(4) 0.0668(10) Uani d . 1
H H28 0.3255 0.0203 0.1630 0.080 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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 '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 C17 93.28(10) y
O1 Sn1 C23 97.24(10) y
C17 Sn1 C23 121.98(11) y
O1 Sn1 O2 157.50(8) y
C17 Sn1 O2 94.95(11) y
C23 Sn1 O2 96.06(11) y
O1 Sn1 N1 82.35(8) y
C17 Sn1 N1 122.87(10) y
C23 Sn1 N1 115.06(10) y
O2 Sn1 N1 75.59(8) y
C7 N1 C8 118.5(2) ?
C7 N1 Sn1 124.2(2) ?
C8 N1 Sn1 115.56(17) ?
C1 O1 Sn1 125.1(2) ?
C9 O2 Sn1 121.04(18) ?
O1 C1 C6 123.0(3) ?
O1 C1 C2 120.1(3) ?
C6 C1 C2 116.9(3) ?
C3 C2 C1 122.1(3) ?
C3 C2 Br1 119.9(3) ?
C1 C2 Br1 117.9(2) ?
C2 C3 C4 119.5(3) ?
C2 C3 H3 120.2 ?
C4 C3 H3 120.2 ?
C5 C4 C3 121.2(3) ?
C5 C4 Br2 118.8(3) ?
C3 C4 Br2 120.0(2) ?
C4 C5 C6 119.4(3) ?
C4 C5 H5 120.3 ?
C6 C5 H5 120.3 ?
C1 C6 C5 120.9(3) ?
C1 C6 C7 123.0(3) ?
C5 C6 C7 116.1(3) ?
N1 C7 C6 127.0(3) ?
N1 C7 H7 116.5 ?
C6 C7 H7 116.5 ?
N1 C8 C10 111.8(2) ?
N1 C8 C9 109.5(2) ?
C10 C8 C9 109.5(2) ?
N1 C8 H8 108.6 ?
C10 C8 H8 108.6 ?
C9 C8 H8 108.6 ?
O3 C9 O2 124.4(3) ?
O3 C9 C8 119.1(3) ?
O2 C9 C8 116.5(3) ?
C11 C10 C8 112.9(3) ?
C11 C10 H10A 109.0 ?
C8 C10 H10A 109.0 ?
C11 C10 H10B 109.0 ?
C8 C10 H10B 109.0 ?
H10A C10 H10B 107.8 ?
C12 C11 C16 117.6(4) ?
C12 C11 C10 121.6(3) ?
C16 C11 C10 120.8(3) ?
C11 C12 C13 121.3(4) ?
C11 C12 H12 119.3 ?
C13 C12 H12 119.3 ?
C14 C13 C12 120.0(5) ?
C14 C13 H13 120.0 ?
C12 C13 H13 120.0 ?
C13 C14 C15 120.2(5) ?
C13 C14 H14 119.9 ?
C15 C14 H14 119.9 ?
C14 C15 C16 119.7(5) ?
C14 C15 H15 120.1 ?
C16 C15 H15 120.1 ?
C11 C16 C15 121.1(5) ?
C11 C16 H16 119.5 ?
C15 C16 H16 119.5 ?
C18 C17 C22 118.3(3) ?
C18 C17 Sn1 120.2(2) ?
C22 C17 Sn1 121.1(3) ?
C17 C18 C19 121.0(4) ?
C17 C18 H18 119.5 ?
C19 C18 H18 119.5 ?
C20 C19 C18 119.8(5) ?
C20 C19 H19 120.1 ?
C18 C19 H19 120.1 ?
C19 C20 C21 120.3(4) ?
C19 C20 H20 119.8 ?
C21 C20 H20 119.8 ?
C20 C21 C22 120.1(4) ?
C20 C21 H21 119.9 ?
C22 C21 H21 119.9 ?
C17 C22 C21 120.5(4) ?
C17 C22 H22 119.8 ?
C21 C22 H22 119.8 ?
C28 C23 C24 118.4(3) ?
C28 C23 Sn1 121.1(2) ?
C24 C23 Sn1 120.4(3) ?
C23 C24 C25 120.4(4) ?
C23 C24 H24 119.8 ?
C25 C24 H24 119.8 ?
C26 C25 C24 119.9(4) ?
C26 C25 H25 120.0 ?
C24 C25 H25 120.0 ?
C25 C26 C27 120.3(4) ?
C25 C26 H26 119.9 ?
C27 C26 H26 119.9 ?
C26 C27 C28 120.0(4) ?
C26 C27 H27 120.0 ?
C28 C27 H27 120.0 ?
C23 C28 C27 121.0(4) ?
C23 C28 H28 119.5 ?
C27 C28 H28 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Sn1 O1 2.095(2) y
Sn1 C17 2.107(3) y
Sn1 C23 2.110(3) y
Sn1 O2 2.114(2) y
Sn1 N1 2.168(2) y
Br2 C4 1.900(3) ?
Br1 C2 1.891(3) ?
N1 C7 1.288(4) ?
N1 C8 1.468(4) ?
O1 C1 1.311(4) ?
O2 C9 1.292(4) ?
O3 C9 1.212(4) ?
C1 C6 1.407(5) ?
C1 C2 1.413(4) ?
C2 C3 1.374(5) ?
C3 C4 1.382(5) ?
C3 H3 0.9300 ?
C4 C5 1.375(4) ?
C5 C6 1.410(4) ?
C5 H5 0.9300 ?
C6 C7 1.440(4) ?
C7 H7 0.9300 ?
C8 C10 1.531(4) ?
C8 C9 1.535(4) ?
C8 H8 0.9800 ?
C10 C11 1.512(4) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.369(5) ?
C11 C16 1.373(5) ?
C12 C13 1.374(6) ?
C12 H12 0.9300 ?
C13 C14 1.350(8) ?
C13 H13 0.9300 ?
C14 C15 1.356(8) ?
C14 H14 0.9300 ?
C15 C16 1.380(7) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 C18 1.371(5) ?
C17 C22 1.376(5) ?
C18 C19 1.383(6) ?
C18 H18 0.9300 ?
C19 C20 1.357(7) ?
C19 H19 0.9300 ?
C20 C21 1.357(7) ?
C20 H20 0.9300 ?
C21 C22 1.385(6) ?
C21 H21 0.9300 ?
C22 H22 0.9300 ?
C23 C28 1.371(5) ?
C23 C24 1.375(5) ?
C24 C25 1.387(5) ?
C24 H24 0.9300 ?
C25 C26 1.356(6) ?
C25 H25 0.9300 ?
C26 C27 1.358(6) ?
C26 H26 0.9300 ?
C27 C28 1.375(5) ?
C27 H27 0.9300 ?
C28 H28 0.9300 ?
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
O1 Sn1 N1 C7 30.4(2)
C17 Sn1 N1 C7 119.4(3)
C23 Sn1 N1 C7 -64.0(3)
O2 Sn1 N1 C7 -154.0(3)
O1 Sn1 N1 C8 -165.0(2)
C17 Sn1 N1 C8 -76.0(2)
C23 Sn1 N1 C8 100.6(2)
O2 Sn1 N1 C8 10.54(19)
C17 Sn1 O1 C1 -165.2(2)
C23 Sn1 O1 C1 72.0(2)
O2 Sn1 O1 C1 -53.8(4)
N1 Sn1 O1 C1 -42.5(2)
O1 Sn1 O2 C9 7.8(4)
C17 Sn1 O2 C9 118.9(2)
C23 Sn1 O2 C9 -118.2(2)
N1 Sn1 O2 C9 -3.8(2)
Sn1 O1 C1 C6 38.0(4)
Sn1 O1 C1 C2 -142.9(2)
O1 C1 C2 C3 -178.2(3)
C6 C1 C2 C3 0.9(5)
O1 C1 C2 Br1 3.6(4)
C6 C1 C2 Br1 -177.3(2)
C1 C2 C3 C4 0.0(5)
Br1 C2 C3 C4 178.2(2)
C2 C3 C4 C5 -0.2(5)
C2 C3 C4 Br2 179.7(2)
C3 C4 C5 C6 -0.5(5)
Br2 C4 C5 C6 179.6(2)
O1 C1 C6 C5 177.5(3)
C2 C1 C6 C5 -1.6(5)
O1 C1 C6 C7 -4.9(5)
C2 C1 C6 C7 176.0(3)
C4 C5 C6 C1 1.4(5)
C4 C5 C6 C7 -176.4(3)
C8 N1 C7 C6 -178.6(3)
Sn1 N1 C7 C6 -14.5(4)
C1 C6 C7 N1 -6.8(5)
C5 C6 C7 N1 170.9(3)
C7 N1 C8 C10 -87.8(3)
Sn1 N1 C8 C10 106.7(2)
C7 N1 C8 C9 150.7(3)
Sn1 N1 C8 C9 -14.8(3)
Sn1 O2 C9 O3 177.3(2)
Sn1 O2 C9 C8 -3.5(3)
N1 C8 C9 O3 -168.8(3)
C10 C8 C9 O3 68.2(4)
N1 C8 C9 O2 11.9(4)
C10 C8 C9 O2 -111.0(3)
N1 C8 C10 C11 65.6(3)
C9 C8 C10 C11 -172.8(3)
C8 C10 C11 C12 56.0(4)
C8 C10 C11 C16 -124.3(3)
C16 C11 C12 C13 1.7(6)
C10 C11 C12 C13 -178.6(4)
C11 C12 C13 C14 -0.4(8)
C12 C13 C14 C15 -1.5(9)
C13 C14 C15 C16 2.1(9)
C12 C11 C16 C15 -1.0(6)
C10 C11 C16 C15 179.2(4)
C14 C15 C16 C11 -0.8(8)
O1 Sn1 C17 C18 -24.7(3)
C23 Sn1 C17 C18 76.0(3)
O2 Sn1 C17 C18 176.3(3)
N1 Sn1 C17 C18 -107.7(3)
O1 Sn1 C17 C22 162.3(3)
C23 Sn1 C17 C22 -97.1(3)
O2 Sn1 C17 C22 3.3(3)
N1 Sn1 C17 C22 79.3(3)
C22 C17 C18 C19 -0.1(6)
Sn1 C17 C18 C19 -173.4(3)
C17 C18 C19 C20 0.3(7)
C18 C19 C20 C21 0.0(8)
C19 C20 C21 C22 -0.5(8)
C18 C17 C22 C21 -0.4(6)
Sn1 C17 C22 C21 172.8(3)
C20 C21 C22 C17 0.7(7)
O1 Sn1 C23 C28 -160.7(3)
C17 Sn1 C23 C28 100.8(3)
O2 Sn1 C23 C28 1.1(3)
N1 Sn1 C23 C28 -75.8(3)
O1 Sn1 C23 C24 22.9(3)
C17 Sn1 C23 C24 -75.6(3)
O2 Sn1 C23 C24 -175.3(3)
N1 Sn1 C23 C24 107.8(3)
C28 C23 C24 C25 -0.1(6)
Sn1 C23 C24 C25 176.5(3)
C23 C24 C25 C26 -1.0(7)
C24 C25 C26 C27 1.8(7)
C25 C26 C27 C28 -1.5(8)
C24 C23 C28 C27 0.4(6)
Sn1 C23 C28 C27 -176.1(4)
C26 C27 C28 C23 0.4(7)
