#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:17:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178697 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/08/4080815.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_4080815
loop_
_publ_author_name
'Arens, Verena'
'Dietz, Christina'
'Schollmeyer, Dieter'
'Jurkschat, Klaus'
_publ_section_title
;
 Intramolecularly Coordinated Bis(crown ether)-Substituted Organotin
 Halides as Ditopic Salt Receptors
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              2775
_journal_paper_doi               10.1021/om400216z
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C24 H46 Br2 O10 Sn'
_chemical_formula_sum            'C24 H46 Br2 O10 Sn'
_chemical_formula_weight         773.12
_chemical_melting_point          396
_chemical_name_systematic
; 
dibromido-bis(1,4,7,10,13-pentaoxacyclohexadec-15-ylmethyl)-stannane 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 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                 100.304(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1335(19)
_cell_length_b                   11.5894(7)
_cell_length_c                   16.415(3)
_cell_measurement_reflns_used    5115
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.0164
_cell_measurement_theta_min      2.5172
_cell_volume                     3019.7(7)
_computing_cell_refinement
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55''
_computing_data_collection
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55''
_computing_data_reduction
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55''
_computing_molecular_graphics    'SHELXP-97 (Sheldrick, 1997)'
_computing_publication_material  'enCIFer Version 1.4'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Xcalibur2 CCD Diffractometer'
_diffrn_measurement_method       'ω und ψ scan'
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9403
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    3.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0239
_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)+(0.0251P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0495
_refine_ls_wR_factor_ref         0.0505
_reflns_number_gt                2135
_reflns_number_total             2814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400216z_si_001.cif
_cod_data_source_block           compound4_a1383i
_cod_original_sg_symbol_H-M      I2/a
_cod_database_code               4080815
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
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 0.2500 0.94917(3) 0.0000 0.01840(9) Uani 1 2 d S
Br1 Br 0.207443(18) 0.79709(3) 0.097436(18) 0.02864(10) Uani 1 1 d .
O1 O 0.23334(10) 1.09141(18) 0.11651(11) 0.0252(5) Uani 1 1 d .
C1 C 0.37306(15) 1.0096(3) 0.05241(17) 0.0189(7) Uani 1 1 d .
H1A H 0.3994 0.9553 0.0961 0.023 Uiso 1 1 calc R
H1B H 0.4084 1.0116 0.0089 0.023 Uiso 1 1 calc R
C2 C 0.36996(16) 1.1289(3) 0.08932(17) 0.0250(7) Uani 1 1 d .
H2A H 0.3464 1.1838 0.0440 0.030 Uiso 1 1 calc R
O2 O 0.24692(12) 1.09638(18) 0.30466(12) 0.0288(5) Uani 1 1 d .
C3 C 0.31559(16) 1.1322(3) 0.15376(17) 0.0265(8) Uani 1 1 d .
H3A H 0.3396 1.0824 0.2011 0.032 Uiso 1 1 calc R
H3B H 0.3119 1.2120 0.1743 0.032 Uiso 1 1 calc R
O3 O 0.41389(12) 1.0991(2) 0.39081(13) 0.0388(6) Uani 1 1 d .
O4 O 0.51953(13) 1.2623(2) 0.32505(13) 0.0388(6) Uani 1 1 d .
C4 C 0.16937(16) 1.1100(3) 0.16646(18) 0.0301(8) Uani 1 1 d .
H4A H 0.1140 1.0884 0.1336 0.036 Uiso 1 1 calc R
H4B H 0.1674 1.1933 0.1794 0.036 Uiso 1 1 calc R
O5 O 0.45174(12) 1.2845(2) 0.15492(12) 0.0324(6) Uani 1 1 d .
C5 C 0.18268(19) 1.0438(3) 0.24555(19) 0.0352(8) Uani 1 1 d .
H5A H 0.1295 1.0413 0.2677 0.042 Uiso 1 1 calc R
H5B H 0.1991 0.9635 0.2352 0.042 Uiso 1 1 calc R
C6 C 0.2754(2) 1.0266(3) 0.3739(2) 0.0407(9) Uani 1 1 d .
H6A H 0.2963 0.9522 0.3559 0.049 Uiso 1 1 calc R
H6B H 0.2283 1.0104 0.4036 0.049 Uiso 1 1 calc R
C7 C 0.3442(2) 1.0869(3) 0.4300(2) 0.0461(10) Uani 1 1 d .
H7A H 0.3246 1.1639 0.4445 0.055 Uiso 1 1 calc R
H7B H 0.3603 1.0421 0.4818 0.055 Uiso 1 1 calc R
C8 C 0.4805(2) 1.1621(3) 0.43843(19) 0.0435(10) Uani 1 1 d .
H8A H 0.5034 1.1190 0.4896 0.052 Uiso 1 1 calc R
H8B H 0.4594 1.2375 0.4545 0.052 Uiso 1 1 calc R
C9 C 0.54753(19) 1.1802(3) 0.3887(2) 0.0440(10) Uani 1 1 d .
H9A H 0.5993 1.2087 0.4247 0.053 Uiso 1 1 calc R
H9B H 0.5609 1.1063 0.3637 0.053 Uiso 1 1 calc R
C10 C 0.57298(18) 1.2725(3) 0.2665(2) 0.0378(9) Uani 1 1 d .
H10A H 0.5898 1.1948 0.2505 0.045 Uiso 1 1 calc R
H10B H 0.6246 1.3150 0.2912 0.045 Uiso 1 1 calc R
C11 C 0.52928(17) 1.3347(3) 0.19202(19) 0.0356(9) Uani 1 1 d .
H11A H 0.5188 1.4152 0.2077 0.043 Uiso 1 1 calc R
H11B H 0.5669 1.3374 0.1506 0.043 Uiso 1 1 calc R
C12 C 0.45854(17) 1.1694(3) 0.12831(18) 0.0274(8) Uani 1 1 d .
H12A H 0.4818 1.1196 0.1759 0.033 Uiso 1 1 calc R
H12B H 0.4965 1.1654 0.0872 0.033 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Sn1 C1 141.74(16) 2 .
C1 Sn1 Br1 98.26(8) 2 .
C1 Sn1 Br1 107.97(8) . .
C1 Sn1 Br1 107.97(8) 2 2
C1 Sn1 Br1 98.26(8) . 2
Br1 Sn1 Br1 92.77(2) . 2
C1 Sn1 O1 82.90(9) 2 .
C1 Sn1 O1 72.79(9) . .
Br1 Sn1 O1 84.33(5) . .
Br1 Sn1 O1 169.08(4) 2 .
C3 O1 C4 114.1(2) . .
C3 O1 Sn1 108.37(15) . .
C4 O1 Sn1 134.19(17) . .
C2 C1 Sn1 111.45(17) . .
C2 C1 H1A 109.3 . .
Sn1 C1 H1A 109.3 . .
C2 C1 H1B 109.3 . .
Sn1 C1 H1B 109.3 . .
H1A C1 H1B 108.0 . .
C3 C2 C1 111.9(3) . .
C3 C2 C12 108.6(2) . .
C1 C2 C12 110.6(2) . .
C3 C2 H2A 108.6 . .
C1 C2 H2A 108.6 . .
C12 C2 H2A 108.6 . .
C6 O2 C5 113.5(2) . .
O1 C3 C2 107.8(2) . .
O1 C3 H3A 110.2 . .
C2 C3 H3A 110.2 . .
O1 C3 H3B 110.2 . .
C2 C3 H3B 110.2 . .
H3A C3 H3B 108.5 . .
C7 O3 C8 113.0(3) . .
C10 O4 C9 113.8(2) . .
O1 C4 C5 114.3(2) . .
O1 C4 H4A 108.7 . .
C5 C4 H4A 108.7 . .
O1 C4 H4B 108.7 . .
C5 C4 H4B 108.7 . .
H4A C4 H4B 107.6 . .
C12 O5 C11 114.2(2) . .
O2 C5 C4 110.3(3) . .
O2 C5 H5A 109.6 . .
C4 C5 H5A 109.6 . .
O2 C5 H5B 109.6 . .
C4 C5 H5B 109.6 . .
H5A C5 H5B 108.1 . .
O2 C6 C7 109.3(3) . .
O2 C6 H6A 109.8 . .
C7 C6 H6A 109.8 . .
O2 C6 H6B 109.8 . .
C7 C6 H6B 109.8 . .
H6A C6 H6B 108.3 . .
O3 C7 C6 109.6(3) . .
O3 C7 H7A 109.7 . .
C6 C7 H7A 109.7 . .
O3 C7 H7B 109.7 . .
C6 C7 H7B 109.7 . .
H7A C7 H7B 108.2 . .
O3 C8 C9 109.0(3) . .
O3 C8 H8A 109.9 . .
C9 C8 H8A 109.9 . .
O3 C8 H8B 109.9 . .
C9 C8 H8B 109.9 . .
H8A C8 H8B 108.3 . .
O4 C9 C8 109.4(3) . .
O4 C9 H9A 109.8 . .
C8 C9 H9A 109.8 . .
O4 C9 H9B 109.8 . .
C8 C9 H9B 109.8 . .
H9A C9 H9B 108.2 . .
O4 C10 C11 110.2(2) . .
O4 C10 H10A 109.6 . .
C11 C10 H10A 109.6 . .
O4 C10 H10B 109.6 . .
C11 C10 H10B 109.6 . .
H10A C10 H10B 108.1 . .
O5 C11 C10 114.1(3) . .
O5 C11 H11A 108.7 . .
C10 C11 H11A 108.7 . .
O5 C11 H11B 108.7 . .
C10 C11 H11B 108.7 . .
H11A C11 H11B 107.6 . .
O5 C12 C2 107.4(2) . .
O5 C12 H12A 110.2 . .
C2 C12 H12A 110.2 . .
O5 C12 H12B 110.2 . .
C2 C12 H12B 110.2 . .
H12A C12 H12B 108.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 C1 2.136(2) 2
Sn1 C1 2.136(2) .
Sn1 Br1 2.5552(4) .
Sn1 Br1 2.5552(4) 2
Sn1 O1 2.5752(19) .
O1 C3 1.438(3) .
O1 C4 1.444(3) .
C1 C2 1.515(4) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.491(4) .
C2 C12 1.531(4) .
C2 H2A 1.0000 .
O2 C6 1.404(4) .
O2 C5 1.424(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
O3 C7 1.399(3) .
O3 C8 1.414(4) .
O4 C10 1.406(4) .
O4 C9 1.424(4) .
C4 C5 1.490(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
O5 C12 1.414(4) .
O5 C11 1.415(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.484(5) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.483(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.485(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
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
C1 Sn1 O1 C3 -150.95(19) 2
C1 Sn1 O1 C3 -0.84(18) .
Br1 Sn1 O1 C3 109.96(17) .
Br1 Sn1 O1 C3 34.9(4) 2
C1 Sn1 O1 C4 51.7(2) 2
C1 Sn1 O1 C4 -158.2(3) .
Br1 Sn1 O1 C4 -47.4(2) .
Br1 Sn1 O1 C4 -122.5(3) 2
C1 Sn1 C1 C2 25.53(17) 2
Br1 Sn1 C1 C2 -105.39(19) .
Br1 Sn1 C1 C2 158.96(18) 2
O1 Sn1 C1 C2 -27.46(18) .
Sn1 C1 C2 C3 57.4(3) .
Sn1 C1 C2 C12 178.67(19) .
C4 O1 C3 C2 -168.9(3) .
Sn1 O1 C3 C2 28.7(3) .
C1 C2 C3 O1 -56.3(3) .
C12 C2 C3 O1 -178.7(2) .
C3 O1 C4 C5 -65.3(3) .
Sn1 O1 C4 C5 91.1(3) .
C6 O2 C5 C4 -167.3(2) .
O1 C4 C5 O2 76.5(3) .
C5 O2 C6 C7 177.8(2) .
C8 O3 C7 C6 176.4(3) .
O2 C6 C7 O3 -65.5(4) .
C7 O3 C8 C9 -174.4(3) .
C10 O4 C9 C8 -170.7(3) .
O3 C8 C9 O4 71.8(4) .
C9 O4 C10 C11 165.2(3) .
C12 O5 C11 C10 -59.5(3) .
O4 C10 C11 O5 -55.6(4) .
C11 O5 C12 C2 -179.5(2) .
C3 C2 C12 O5 -61.8(3) .
C1 C2 C12 O5 175.0(2) .
