#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:01:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180368 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/37/7203719.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_7203719
loop_
_publ_author_name
'John Fawcett'
'Eric G. Hope'
'Alison M. Stuart'
'Andrew J. West'
_publ_section_title
;
 Recycling of a perfluoroalkylated BINOL ligand using fluorous
 solid-phase extraction
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              316
_journal_paper_doi               10.1039/b418039a
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C32 H40 O2 Sn'
_chemical_formula_weight         575.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 115.519(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.2787(12)
_cell_length_b                   11.6990(13)
_cell_length_c                   11.6960(13)
_cell_measurement_reflns_used    7853
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.60
_cell_volume                     1392.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10765
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction based on 9841 reflections (SADABS); Rint 0.036 before
correction and 0.030 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         3.941
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5207
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0450
_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)+(0.0905P)²+0.3404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                5031
_reflns_number_total             5207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b418039a.txt
_cod_data_source_block           04004
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7203719
loop_
_symmetry_equiv_pos_as_xyz
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.09564(2) 0.87379(5) 0.49311(2) 0.01679(11) Uani 1 1 d . . .
O1 O -0.0531(4) 0.5809(3) 0.5814(3) 0.0215(8) Uani 1 1 d . . .
O2 O 0.1214(4) 0.7026(3) 0.5647(3) 0.0207(8) Uani 1 1 d . . .
C1 C -0.0787(6) 0.8297(5) 0.3288(5) 0.0232(11) Uani 1 1 d . . .
H1A H -0.0936 0.8885 0.2656 0.028 Uiso 1 1 calc R . .
H1B H -0.0615 0.7590 0.2951 0.028 Uiso 1 1 calc R . .
C2 C -0.2068(6) 0.8140(5) 0.3427(6) 0.0305(13) Uani 1 1 d . . .
H2A H -0.1912 0.7633 0.4134 0.037 Uiso 1 1 calc R . .
H2B H -0.2348 0.8874 0.3612 0.037 Uiso 1 1 calc R . .
C3 C -0.3149(6) 0.7649(5) 0.2235(6) 0.0328(14) Uani 1 1 d . . .
H3A H -0.3273 0.8146 0.1529 0.039 Uiso 1 1 calc R . .
H3B H -0.2867 0.6910 0.2068 0.039 Uiso 1 1 calc R . .
C4 C -0.4451(6) 0.7506(7) 0.2296(7) 0.0458(19) Uani 1 1 d . . .
H4A H -0.4311 0.7160 0.3088 0.069 Uiso 1 1 d R . .
H4B H -0.5015 0.7027 0.1611 0.069 Uiso 1 1 d R . .
H4C H -0.4855 0.8241 0.2227 0.069 Uiso 1 1 d R . .
C5 C 0.1040(6) 0.9515(5) 0.6622(5) 0.0224(11) Uani 1 1 d . . .
H5A H 0.1558 0.9030 0.7337 0.027 Uiso 1 1 calc R . .
H5B H 0.1492 1.0241 0.6745 0.027 Uiso 1 1 calc R . .
C6 C -0.0285(6) 0.9719(5) 0.6625(5) 0.0240(12) Uani 1 1 d . . .
H6A H -0.0731 0.8993 0.6536 0.029 Uiso 1 1 calc R . .
H6B H -0.0817 1.0190 0.5902 0.029 Uiso 1 1 calc R . .
C7 C -0.0163(6) 1.0307(5) 0.7838(6) 0.0259(12) Uani 1 1 d . . .
H7A H 0.0313 0.9811 0.8556 0.031 Uiso 1 1 calc R . .
H7B H 0.0338 1.1007 0.7959 0.031 Uiso 1 1 calc R . .
C8 C -0.1479(8) 1.0583(7) 0.7795(8) 0.0373(19) Uani 1 1 d . . .
H8A H -0.1950 1.1080 0.7092 0.056 Uiso 1 1 d R . .
H8B H -0.1361 1.0955 0.8568 0.056 Uiso 1 1 d R . .
H8C H -0.1969 0.9890 0.7699 0.056 Uiso 1 1 d R . .
C9 C 0.2701(5) 0.8887(6) 0.4599(5) 0.0197(13) Uani 1 1 d . . .
H9A H 0.3027 0.8128 0.4556 0.024 Uiso 1 1 calc R . .
H9B H 0.2470 0.9257 0.3789 0.024 Uiso 1 1 calc R . .
C10 C 0.3775(6) 0.9561(6) 0.5623(6) 0.0308(13) Uani 1 1 d . . .
H10A H 0.4060 0.9150 0.6418 0.037 Uiso 1 1 calc R . .
H10B H 0.3418 1.0289 0.5724 0.037 Uiso 1 1 calc R . .
C11 C 0.4952(7) 0.9781(7) 0.5358(8) 0.0460(18) Uani 1 1 d . . .
H11A H 0.5542 1.0310 0.5982 0.055 Uiso 1 1 calc R . .
H11B H 0.4665 1.0129 0.4528 0.055 Uiso 1 1 calc R . .
C12 C 0.5678(6) 0.8675(15) 0.5400(9) 0.071(3) Uani 1 1 d . . .
H12A H 0.6454 0.8631 0.6187 0.106 Uiso 1 1 d R . .
H12B H 0.5921 0.8660 0.4708 0.106 Uiso 1 1 d R . .
H12C H 0.5118 0.8036 0.5333 0.106 Uiso 1 1 d R . .
C13 C -0.0421(6) 0.6322(4) 0.6921(5) 0.0198(11) Uani 1 1 d . . .
C14 C -0.1604(6) 0.6512(5) 0.7025(6) 0.0237(12) Uani 1 1 d . . .
H14 H -0.2396 0.6288 0.6369 0.028 Uiso 1 1 calc R . .
C15 C -0.1605(6) 0.7022(6) 0.8080(6) 0.0236(14) Uani 1 1 d . . .
H15 H -0.2381 0.7093 0.8172 0.028 Uiso 1 1 calc R . .
C16 C -0.0398(5) 0.7442(5) 0.9033(5) 0.0213(11) Uani 1 1 d . . .
C17 C -0.0397(6) 0.8081(5) 1.0052(6) 0.0261(12) Uani 1 1 d . . .
H17 H -0.1180 0.8179 1.0125 0.031 Uiso 1 1 calc R . .
C18 C 0.0735(6) 0.8562(6) 1.0942(5) 0.0284(14) Uani 1 1 d . . .
H18 H 0.0722 0.8973 1.1617 0.034 Uiso 1 1 calc R . .
C19 C 0.1903(6) 0.8427(5) 1.0820(6) 0.0274(14) Uani 1 1 d . . .
H19 H 0.2668 0.8766 1.1411 0.033 Uiso 1 1 calc R . .
C20 C 0.1944(5) 0.7800(5) 0.9837(6) 0.0231(12) Uani 1 1 d . . .
H20 H 0.2735 0.7718 0.9776 0.028 Uiso 1 1 calc R . .
C21 C 0.0785(5) 0.7278(4) 0.8915(5) 0.0182(10) Uani 1 1 d . . .
C22 C 0.0793(5) 0.6628(5) 0.7861(5) 0.0198(11) Uani 1 1 d . . .
C23 C 0.2038(5) 0.6352(4) 0.7784(5) 0.0193(11) Uani 1 1 d . . .
C24 C 0.2233(5) 0.6622(4) 0.6708(5) 0.0184(10) Uani 1 1 d . . .
C25 C 0.3449(6) 0.6456(5) 0.6689(6) 0.0241(12) Uani 1 1 d . . .
H25 H 0.3556 0.6668 0.5973 0.029 Uiso 1 1 calc R . .
C26 C 0.4489(6) 0.5990(5) 0.7701(6) 0.0300(13) Uani 1 1 d . . .
H26 H 0.5303 0.5921 0.7684 0.036 Uiso 1 1 calc R . .
C27 C 0.4320(6) 0.5612(5) 0.8769(5) 0.0235(12) Uani 1 1 d . . .
C28 C 0.5344(6) 0.5029(5) 0.9790(6) 0.0276(13) Uani 1 1 d . . .
H28 H 0.6167 0.4964 0.9792 0.033 Uiso 1 1 calc R . .
C29 C 0.5144(6) 0.4568(6) 1.0756(5) 0.0312(14) Uani 1 1 d . . .
H29 H 0.5817 0.4177 1.1405 0.037 Uiso 1 1 calc R . .
C30 C 0.3914(6) 0.4688(5) 1.0764(5) 0.0281(13) Uani 1 1 d . . .
H30 H 0.3778 0.4372 1.1427 0.034 Uiso 1 1 calc R . .
C31 C 0.2902(6) 0.5259(5) 0.9819(5) 0.0224(11) Uani 1 1 d . . .
H31 H 0.2095 0.5321 0.9851 0.027 Uiso 1 1 calc R . .
C32 C 0.3075(5) 0.5756(5) 0.8793(5) 0.0191(10) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Sn1 O2 92.45(19) . . y
C1 Sn1 C5 126.2(2) . . y
O2 Sn1 C5 95.24(18) . . y
C1 Sn1 C9 114.3(2) . . y
O2 Sn1 C9 99.4(2) . . y
C5 Sn1 C9 116.7(2) . . y
C1 Sn1 O1 87.55(18) . 2_556 y
O2 Sn1 O1 175.01(13) . 2_556 y
C5 Sn1 O1 80.77(17) . 2_556 y
C9 Sn1 O1 85.1(2) . 2_556 ?
C13 O1 Sn1 131.3(3) . 2_546 ?
C24 O2 Sn1 126.9(3) . . ?
C2 C1 Sn1 118.5(4) . . ?
C3 C2 C1 111.6(5) . . ?
C4 C3 C2 114.4(6) . . ?
C6 C5 Sn1 114.7(4) . . ?
C5 C6 C7 112.2(5) . . ?
C8 C7 C6 112.0(5) . . ?
C10 C9 Sn1 112.3(4) . . ?
C9 C10 C11 113.7(5) . . ?
C10 C11 C12 111.0(7) . . ?
O1 C13 C22 121.0(5) . . ?
O1 C13 C14 116.3(5) . . ?
C22 C13 C14 122.7(5) . . ?
C15 C14 C13 121.0(5) . . ?
C14 C15 C16 118.9(5) . . ?
C17 C16 C21 120.0(5) . . ?
C17 C16 C15 119.8(5) . . ?
C21 C16 C15 120.1(5) . . ?
C18 C17 C16 121.4(5) . . ?
C17 C18 C19 119.2(5) . . ?
C20 C19 C18 121.1(5) . . ?
C19 C20 C21 120.6(5) . . ?
C16 C21 C20 117.7(5) . . ?
C16 C21 C22 120.4(5) . . ?
C20 C21 C22 121.8(5) . . ?
C13 C22 C21 116.3(5) . . ?
C13 C22 C23 122.3(5) . . ?
C21 C22 C23 121.3(5) . . ?
C24 C23 C32 117.4(5) . . ?
C24 C23 C22 121.6(5) . . ?
C32 C23 C22 120.9(5) . . ?
O2 C24 C25 118.9(5) . . ?
O2 C24 C23 119.9(5) . . ?
C25 C24 C23 121.2(5) . . ?
C26 C25 C24 121.5(5) . . ?
C25 C26 C27 119.8(5) . . ?
C26 C27 C32 119.3(5) . . ?
C26 C27 C28 121.3(5) . . ?
C32 C27 C28 119.3(5) . . ?
C29 C28 C27 121.4(5) . . ?
C28 C29 C30 119.2(5) . . ?
C31 C30 C29 121.8(5) . . ?
C30 C31 C32 120.7(5) . . ?
C31 C32 C27 117.5(5) . . ?
C31 C32 C23 122.3(5) . . ?
C27 C32 C23 120.1(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 C1 2.138(5) . y
Sn1 O2 2.142(4) . y
Sn1 C5 2.142(5) . y
Sn1 C9 2.171(5) . y
Sn1 O1 2.549(4) 2_556 y
O1 C13 1.383(7) . y
O1 Sn1 2.549(4) 2_546 y
O2 C24 1.363(6) . y
C1 C2 1.533(8) . ?
C2 C3 1.515(8) . ?
C3 C4 1.510(10) . ?
C5 C6 1.514(8) . ?
C6 C7 1.529(8) . ?
C7 C8 1.498(9) . ?
C9 C10 1.508(8) . ?
C10 C11 1.510(9) . ?
C11 C12 1.520(16) . ?
C13 C22 1.384(8) . ?
C13 C14 1.409(8) . ?
C14 C15 1.372(8) . ?
C15 C16 1.425(8) . ?
C16 C17 1.407(8) . ?
C16 C21 1.412(7) . ?
C17 C18 1.373(8) . ?
C18 C19 1.394(8) . ?
C19 C20 1.382(8) . ?
C20 C21 1.425(8) . ?
C21 C22 1.452(8) . ?
C22 C23 1.481(8) . ?
C23 C24 1.403(7) . ?
C23 C32 1.434(8) . ?
C24 C25 1.394(8) . ?
C25 C26 1.371(8) . ?
C26 C27 1.414(8) . ?
C27 C32 1.426(8) . ?
C27 C28 1.427(8) . ?
C28 C29 1.356(9) . ?
C29 C30 1.398(9) . ?
C30 C31 1.372(8) . ?
C31 C32 1.421(7) . ?
