#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/33/4073393.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_4073393
loop_
_publ_author_name
'Reeske, Gregor'
'Schürmann, Markus'
'Costisella, Burkhard'
'Jurkschat, Klaus'
_publ_section_title
;
 Ph(3-n)XnSnCH2-16-crown-5 (X = F, Cl, Br, I, SCN;n= 1, 2): 
 Intramolecular O → Sn Coordination versus Ditopic Complexation
 of Sodium Thiocyanate†
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4170
_journal_paper_doi               10.1021/om700304p
_journal_volume                  26
_journal_year                    2007
_chemical_formula_moiety         '? C24 H33 Br O5 Sn, 0.5 C H2 Cl2'
_chemical_formula_sum            'C24.5 H34 Br Cl O5 Sn'
_chemical_formula_weight         642.57
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_cell_angle_alpha                114.571(5)
_cell_angle_beta                 99.533(4)
_cell_angle_gamma                96.655(5)
_cell_formula_units_Z            2
_cell_length_a                   9.3718(8)
_cell_length_b                   12.6614(7)
_cell_length_c                   12.744(1)
_cell_measurement_reflns_used    15271
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.99
_cell_volume                     1327.19(18)
_computing_cell_refinement
;
DENZO & SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO & SCALEPACK
;
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material
;
SHELXL97
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean '19 vertical, 18 horizontal'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method
;
 4 sets at different κ-angles and 182 frames via ω-rotation 
(Δ/ω=2°) at two times 7,5s per frame
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15271
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    2.600
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;?  
 ? 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             646
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.813
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0264
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0451
_reflns_number_gt                4250
_reflns_number_total             5939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700304p-file003.cif
_cod_data_source_block           compound3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1327.2(2)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C24.50 H34 Br Cl O5 Sn'
_cod_database_code               4073393
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 0.015046(17) 0.258786(15) 0.397382(15) 0.01948(5) Uani 1 1 d .
Br1 Br -0.12103(3) 0.28646(2) 0.21753(2) 0.02934(8) Uani 1 1 d .
O1 O 0.17598(16) 0.27318(14) 0.58820(13) 0.0211(4) Uani 1 1 d .
C1 C -0.1733(2) 0.2408(2) 0.4680(2) 0.0213(6) Uani 1 1 d .
O2 O 0.35050(17) 0.25531(15) 0.80000(14) 0.0296(4) Uani 1 1 d .
C2 C -0.2935(3) 0.1503(2) 0.3965(2) 0.0330(7) Uani 1 1 d .
H2A H -0.2887 0.0967 0.3211 0.040 Uiso 1 1 calc R
O3 O 0.65626(18) 0.36546(16) 0.91554(14) 0.0322(4) Uani 1 1 d .
C3 C -0.4218(3) 0.1379(3) 0.4356(3) 0.0410(8) Uani 1 1 d .
H3A H -0.5025 0.0772 0.3861 0.049 Uiso 1 1 calc R
O4 O 0.70143(18) 0.58173(16) 0.90177(15) 0.0357(5) Uani 1 1 d .
C4 C -0.4287(3) 0.2160(2) 0.5477(2) 0.0333(7) Uani 1 1 d .
H4A H -0.5140 0.2074 0.5743 0.040 Uiso 1 1 calc R
O5 O 0.54567(16) 0.54781(14) 0.68000(14) 0.0253(4) Uani 1 1 d .
C5 C -0.3100(3) 0.3064(2) 0.6205(2) 0.0288(6) Uani 1 1 d .
H5A H -0.3150 0.3594 0.6961 0.035 Uiso 1 1 calc R
C6 C -0.1828(2) 0.3185(2) 0.5809(2) 0.0232(6) Uani 1 1 d .
H6A H -0.1026 0.3796 0.6306 0.028 Uiso 1 1 calc R
C7 C 0.0736(2) 0.0921(2) 0.3006(2) 0.0209(6) Uani 1 1 d .
C8 C 0.1584(3) 0.0399(2) 0.3584(2) 0.0290(6) Uani 1 1 d .
H8A H 0.1944 0.0799 0.4403 0.035 Uiso 1 1 calc R
C9 C 0.1904(3) -0.0703(2) 0.2964(3) 0.0341(7) Uani 1 1 d .
H9A H 0.2472 -0.1032 0.3372 0.041 Uiso 1 1 calc R
C10 C 0.1390(3) -0.1313(2) 0.1756(3) 0.0386(7) Uani 1 1 d .
H10A H 0.1610 -0.2051 0.1340 0.046 Uiso 1 1 calc R
C11 C 0.0539(3) -0.0817(2) 0.1162(2) 0.0411(7) Uani 1 1 d .
H11A H 0.0182 -0.1224 0.0343 0.049 Uiso 1 1 calc R
C12 C 0.0214(3) 0.0289(2) 0.1786(2) 0.0321(6) Uani 1 1 d .
H12A H -0.0363 0.0610 0.1376 0.039 Uiso 1 1 calc R
C21 C 0.1692(2) 0.4237(2) 0.4773(2) 0.0206(6) Uani 1 1 d .
H21A H 0.1955 0.4415 0.4150 0.025 Uiso 1 1 calc R
H21B H 0.1218 0.4857 0.5231 0.025 Uiso 1 1 calc R
C22 C 0.3100(2) 0.4264(2) 0.55807(19) 0.0180(5) Uani 1 1 d .
H22A H 0.3645 0.3708 0.5099 0.022 Uiso 1 1 calc R
C23 C 0.2741(2) 0.3894(2) 0.6513(2) 0.0220(6) Uani 1 1 d .
H23A H 0.3639 0.3854 0.6987 0.026 Uiso 1 1 calc R
H23B H 0.2261 0.4462 0.7037 0.026 Uiso 1 1 calc R
C24 C 0.1239(2) 0.2267(2) 0.6639(2) 0.0254(6) Uani 1 1 d .
H24A H 0.0321 0.1692 0.6196 0.030 Uiso 1 1 calc R
H24B H 0.1026 0.2909 0.7304 0.030 Uiso 1 1 calc R
C25 C 0.2315(2) 0.1684(2) 0.7110(2) 0.0275(6) Uani 1 1 d .
H25A H 0.1816 0.1222 0.7439 0.033 Uiso 1 1 calc R
H25B H 0.2689 0.1149 0.6468 0.033 Uiso 1 1 calc R
C26 C 0.4530(3) 0.2044(3) 0.8501(2) 0.0386(7) Uani 1 1 d .
H26A H 0.5036 0.1590 0.7912 0.046 Uiso 1 1 calc R
H26B H 0.4008 0.1510 0.8745 0.046 Uiso 1 1 calc R
C27 C 0.5627(3) 0.3006(3) 0.9547(2) 0.0386(7) Uani 1 1 d .
H27A H 0.5115 0.3532 1.0080 0.046 Uiso 1 1 calc R
H27B H 0.6213 0.2664 0.9976 0.046 Uiso 1 1 calc R
C28 C 0.7413(3) 0.4724(2) 1.0107(2) 0.0382(7) Uani 1 1 d .
H28A H 0.8157 0.4551 1.0605 0.046 Uiso 1 1 calc R
H28B H 0.6780 0.5152 1.0590 0.046 Uiso 1 1 calc R
C29 C 0.8138(3) 0.5462(3) 0.9605(2) 0.0407(7) Uani 1 1 d .
H29A H 0.8826 0.6154 1.0237 0.049 Uiso 1 1 calc R
H29B H 0.8680 0.5004 0.9050 0.049 Uiso 1 1 calc R
C30 C 0.7542(3) 0.6431(3) 0.8407(2) 0.0374(7) Uani 1 1 d .
H30A H 0.8126 0.5976 0.7892 0.045 Uiso 1 1 calc R
H30B H 0.8164 0.7193 0.8971 0.045 Uiso 1 1 calc R
C31 C 0.6246(3) 0.6610(2) 0.7689(2) 0.0304(6) Uani 1 1 d .
H31A H 0.5613 0.7004 0.8192 0.036 Uiso 1 1 calc R
H31B H 0.6580 0.7101 0.7325 0.036 Uiso 1 1 calc R
C32 C 0.4065(2) 0.5510(2) 0.6177(2) 0.0215(6) Uani 1 1 d .
H32A H 0.4205 0.5778 0.5583 0.026 Uiso 1 1 calc R
H32B H 0.3589 0.6059 0.6725 0.026 Uiso 1 1 calc R
C41 C 0.5448(11) 0.0518(6) 0.0598(6) 0.087(3) Uani 0.50 1 d P
H41A H 0.5949 0.0304 0.1188 0.105 Uiso 0.50 1 calc PR
H41B H 0.5795 0.1361 0.0868 0.105 Uiso 0.50 1 calc PR
Cl1 Cl 0.3699(7) 0.0259(5) 0.0499(7) 0.158(3) Uani 0.50 1 d P
Cl2 Cl 0.5916(7) -0.0275(5) -0.0765(7) 0.109(2) Uani 0.50 1 d P
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'
Cl Cl 0.1484 0.1585 '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
C21 Sn1 C1 119.55(9) . .
C21 Sn1 C7 122.93(8) . .
C1 Sn1 C7 112.86(8) . .
C21 Sn1 O1 72.79(7) . .
C1 Sn1 O1 87.79(7) . .
C7 Sn1 O1 88.79(7) . .
C21 Sn1 Br1 96.09(6) . .
C1 Sn1 Br1 97.03(6) . .
C7 Sn1 Br1 98.54(6) . .
O1 Sn1 Br1 168.82(3) . .
C24 O1 C23 114.48(16) . .
C24 O1 Sn1 124.50(12) . .
C23 O1 Sn1 109.02(12) . .
C2 C1 C6 118.2(2) . .
C2 C1 Sn1 118.49(18) . .
C6 C1 Sn1 123.22(17) . .
C25 O2 C26 112.17(19) . .
C1 C2 C3 121.0(2) . .
C28 O3 C27 111.88(19) . .
C4 C3 C2 119.7(3) . .
C30 O4 C29 113.40(18) . .
C5 C4 C3 120.2(2) . .
C31 O5 C32 113.23(18) . .
C4 C5 C6 119.7(2) . .
C5 C6 C1 121.1(2) . .
C12 C7 C8 117.3(2) . .
C12 C7 Sn1 121.11(17) . .
C8 C7 Sn1 121.51(18) . .
C9 C8 C7 121.5(2) . .
C10 C9 C8 120.5(2) . .
C9 C10 C11 119.1(3) . .
C10 C11 C12 120.3(3) . .
C7 C12 C11 121.3(2) . .
C22 C21 Sn1 114.10(15) . .
C23 C22 C21 110.78(17) . .
C23 C22 C32 110.12(18) . .
C21 C22 C32 109.53(18) . .
O1 C23 C22 106.89(17) . .
O1 C24 C25 113.93(18) . .
O2 C25 C24 110.2(2) . .
O2 C26 C27 109.5(2) . .
O3 C27 C26 109.4(2) . .
O3 C28 C29 108.6(2) . .
O4 C29 C28 107.7(2) . .
O4 C30 C31 108.59(19) . .
O5 C31 C30 107.9(2) . .
O5 C32 C22 108.56(18) . .
Cl1 C41 Cl2 112.7(6) . .
Cl2 Cl1 C41 48.1(17) 2_655 .
Cl2 Cl1 C41 88.2(18) 2_655 2_655
C41 Cl1 C41 55.4(5) . 2_655
Cl1 Cl2 C41 118(2) 2_655 2_655
Cl1 Cl2 C41 77.2(19) 2_655 .
C41 Cl2 C41 57.9(6) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 C21 2.129(2) .
Sn1 C1 2.140(2) .
Sn1 C7 2.146(2) .
Sn1 O1 2.5641(15) .
Sn1 Br1 2.6088(4) .
O1 C24 1.441(2) .
O1 C23 1.455(3) .
C1 C2 1.381(3) .
C1 C6 1.389(3) .
O2 C25 1.414(3) .
O2 C26 1.424(3) .
C2 C3 1.391(3) .
O3 C28 1.416(3) .
O3 C27 1.419(3) .
C3 C4 1.376(4) .
O4 C30 1.412(3) .
O4 C29 1.414(3) .
C4 C5 1.375(3) .
O5 C31 1.418(3) .
O5 C32 1.425(2) .
C5 C6 1.386(3) .
C7 C12 1.386(3) .
C7 C8 1.394(3) .
C8 C9 1.385(3) .
C9 C10 1.371(3) .
C10 C11 1.384(4) .
C11 C12 1.392(4) .
C21 C22 1.521(3) .
C22 C23 1.518(3) .
C22 C32 1.526(3) .
C24 C25 1.504(3) .
C26 C27 1.491(4) .
C28 C29 1.497(3) .
C30 C31 1.494(3) .
C41 Cl1 1.607(12) .
C41 Cl2 1.767(11) .
Cl1 Cl2 0.445(11) 2_655
Cl1 C41 1.724(13) 2_655
Cl2 Cl1 0.445(11) 2_655
Cl2 C41 1.351(11) 2_655
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_4
C21 Sn1 O1 C24 145.39(17) .
C1 Sn1 O1 C24 23.48(17) .
C7 Sn1 O1 C24 -89.45(17) .
Br1 Sn1 O1 C24 139.34(17) .
C21 Sn1 O1 C23 5.15(13) .
C1 Sn1 O1 C23 -116.77(14) .
C7 Sn1 O1 C23 130.30(13) .
Br1 Sn1 O1 C23 -0.9(3) .
C21 Sn1 C1 C2 159.84(17) .
C7 Sn1 C1 C2 -43.6(2) .
O1 Sn1 C1 C2 -131.39(18) .
Br1 Sn1 C1 C2 58.74(18) .
C21 Sn1 C1 C6 -17.6(2) .
C7 Sn1 C1 C6 138.88(18) .
O1 Sn1 C1 C6 51.12(19) .
Br1 Sn1 C1 C6 -118.75(18) .
C6 C1 C2 C3 0.9(4) .
Sn1 C1 C2 C3 -176.73(19) .
C1 C2 C3 C4 -0.9(4) .
C2 C3 C4 C5 0.6(4) .
C3 C4 C5 C6 -0.3(4) .
C4 C5 C6 C1 0.3(3) .
C2 C1 C6 C5 -0.6(3) .
Sn1 C1 C6 C5 176.89(16) .
C21 Sn1 C7 C12 -110.31(19) .
C1 Sn1 C7 C12 94.08(19) .
O1 Sn1 C7 C12 -178.83(19) .
Br1 Sn1 C7 C12 -7.31(19) .
C21 Sn1 C7 C8 73.3(2) .
C1 Sn1 C7 C8 -82.28(19) .
O1 Sn1 C7 C8 4.81(18) .
Br1 Sn1 C7 C8 176.33(17) .
C12 C7 C8 C9 0.4(3) .
Sn1 C7 C8 C9 176.94(17) .
C7 C8 C9 C10 0.1(4) .
C8 C9 C10 C11 -0.4(4) .
C9 C10 C11 C12 0.2(4) .
C8 C7 C12 C11 -0.6(4) .
Sn1 C7 C12 C11 -177.16(18) .
C10 C11 C12 C7 0.3(4) .
C1 Sn1 C21 C22 101.66(17) .
C7 Sn1 C21 C22 -52.40(19) .
O1 Sn1 C21 C22 24.48(14) .
Br1 Sn1 C21 C22 -156.70(15) .
Sn1 C21 C22 C23 -53.9(2) .
Sn1 C21 C22 C32 -175.60(14) .
C24 O1 C23 C22 -176.87(17) .
Sn1 O1 C23 C22 -32.26(18) .
C21 C22 C23 O1 55.6(2) .
C32 C22 C23 O1 176.97(17) .
C23 O1 C24 C25 -82.0(2) .
Sn1 O1 C24 C25 139.63(16) .
C26 O2 C25 C24 178.1(2) .
O1 C24 C25 O2 73.5(3) .
C25 O2 C26 C27 -171.6(2) .
C28 O3 C27 C26 167.4(2) .
O2 C26 C27 O3 -69.8(3) .
C27 O3 C28 C29 -169.1(2) .
C30 O4 C29 C28 -174.5(2) .
O3 C28 C29 O4 67.1(3) .
C29 O4 C30 C31 172.2(2) .
C32 O5 C31 C30 170.37(18) .
O4 C30 C31 O5 -65.6(3) .
C31 O5 C32 C22 -160.30(17) .
C23 C22 C32 O5 65.7(2) .
C21 C22 C32 O5 -172.25(17) .
Cl2 C41 Cl1 Cl2 134.3(18) 2_655
Cl2 C41 Cl1 C41 9.6(3) 2_655
Cl1 C41 Cl2 Cl1 -146.8(12) 2_655
Cl1 C41 Cl2 C41 -12.0(4) 2_655
