#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/33/4073394.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_4073394
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 Cl O5 Sn, 0.5 C H2 Cl2'
_chemical_formula_sum            'C24.5 H34 Cl2 O5 Sn'
_chemical_formula_weight         598.11
_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                114.544(3)
_cell_angle_beta                 99.695(2)
_cell_angle_gamma                96.533(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3160(6)
_cell_length_b                   12.6372(6)
_cell_length_c                   12.7260(8)
_cell_measurement_reflns_used    17271
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.92
_cell_volume                     1314.87(14)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method
;
 4 sets at different κ-angles and 419 frames via ω-rotation 
(Δ/ω=1°) at two times 15s per frame
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17271
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    1.206
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0253
_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          0.0412
_refine_ls_wR_factor_ref         0.0424
_reflns_number_gt                4592
_reflns_number_total             6001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700304p-file003.cif
_cod_data_source_block           compound4
_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        1314.9(1)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C24.50 H34 Cl2 O5 Sn'
_cod_database_code               4073394
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 -0.013989(15) 0.238875(11) 0.100814(12) 0.02224(5) Uani 1 1 d .
Cl1 Cl 0.11560(5) 0.21326(4) 0.27060(4) 0.03291(13) Uani 1 1 d .
O1 O -0.17768(13) 0.22632(10) -0.08968(10) 0.0232(3) Uani 1 1 d .
O2 O -0.35193(15) 0.24358(11) -0.30290(11) 0.0317(3) Uani 1 1 d .
O3 O -0.65923(15) 0.13312(11) -0.41902(11) 0.0340(3) Uani 1 1 d .
O4 O -0.70895(15) -0.08300(12) -0.40271(12) 0.0369(4) Uani 1 1 d .
O5 O -0.54878(14) -0.04853(10) -0.18134(11) 0.0285(3) Uani 1 1 d .
C1 C 0.1744(2) 0.25842(15) 0.03094(17) 0.0231(4) Uani 1 1 d .
C2 C 0.2956(2) 0.34922(17) 0.10293(19) 0.0357(5) Uani 1 1 d .
H2A H 0.2914 0.4018 0.1790 0.043 Uiso 1 1 calc R
C3 C 0.4232(2) 0.36308(18) 0.0635(2) 0.0441(6) Uani 1 1 d .
H3A H 0.5035 0.4247 0.1132 0.053 Uiso 1 1 calc R
C4 C 0.4318(2) 0.28629(18) -0.0485(2) 0.0368(5) Uani 1 1 d .
H4A H 0.5177 0.2958 -0.0746 0.044 Uiso 1 1 calc R
C5 C 0.3122(2) 0.19487(17) -0.12236(18) 0.0308(5) Uani 1 1 d .
H5A H 0.3173 0.1425 -0.1983 0.037 Uiso 1 1 calc R
C6 C 0.1849(2) 0.18162(16) -0.08267(17) 0.0260(5) Uani 1 1 d .
H6A H 0.1046 0.1202 -0.1329 0.031 Uiso 1 1 calc R
C7 C -0.0719(2) 0.40586(15) 0.19865(16) 0.0228(4) Uani 1 1 d .
C8 C -0.1568(2) 0.45937(16) 0.14282(18) 0.0304(5) Uani 1 1 d .
H8A H -0.1941 0.4202 0.0608 0.036 Uiso 1 1 calc R
C9 C -0.1876(2) 0.57029(17) 0.2067(2) 0.0370(6) Uani 1 1 d .
H9A H -0.2450 0.6044 0.1672 0.044 Uiso 1 1 calc R
C10 C -0.1337(2) 0.62962(18) 0.3276(2) 0.0422(6) Uani 1 1 d .
H10A H -0.1542 0.7038 0.3705 0.051 Uiso 1 1 calc R
C11 C -0.0489(3) 0.57831(19) 0.3849(2) 0.0478(6) Uani 1 1 d .
H11A H -0.0120 0.6180 0.4670 0.057 Uiso 1 1 calc R
C12 C -0.0179(2) 0.46725(17) 0.32085(18) 0.0363(5) Uani 1 1 d .
H12A H 0.0398 0.4337 0.3607 0.044 Uiso 1 1 calc R
C21 C -0.1692(2) 0.07352(15) 0.01963(16) 0.0232(4) Uani 1 1 d .
H21A H -0.1213 0.0117 -0.0265 0.028 Uiso 1 1 calc R
H21B H -0.1954 0.0551 0.0816 0.028 Uiso 1 1 calc R
C22 C -0.3110(2) 0.07111(15) -0.06115(15) 0.0206(4) Uani 1 1 d .
H22A H -0.3658 0.1263 -0.0124 0.025 Uiso 1 1 calc R
C23 C -0.2760(2) 0.10964(15) -0.15386(16) 0.0233(4) Uani 1 1 d .
H23A H -0.2276 0.0534 -0.2069 0.028 Uiso 1 1 calc R
H23B H -0.3668 0.1139 -0.2008 0.028 Uiso 1 1 calc R
C24 C -0.1255(2) 0.27381(16) -0.16486(17) 0.0271(5) Uani 1 1 d .
H24A H -0.1031 0.2099 -0.2313 0.032 Uiso 1 1 calc R
H24B H -0.0336 0.3317 -0.1198 0.032 Uiso 1 1 calc R
C25 C -0.2330(2) 0.33158(16) -0.21255(17) 0.0298(5) Uani 1 1 d .
H25A H -0.2717 0.3847 -0.1488 0.036 Uiso 1 1 calc R
H25B H -0.1825 0.3782 -0.2449 0.036 Uiso 1 1 calc R
C26 C -0.4537(2) 0.29342(19) -0.3559(2) 0.0409(6) Uani 1 1 d .
H26A H -0.4003 0.3447 -0.3821 0.049 Uiso 1 1 calc R
H26B H -0.5044 0.3410 -0.2980 0.049 Uiso 1 1 calc R
C27 C -0.5653(2) 0.19560(19) -0.46004(19) 0.0391(6) Uani 1 1 d .
H27A H -0.6242 0.2288 -0.5044 0.047 Uiso 1 1 calc R
H27B H -0.5143 0.1416 -0.5126 0.047 Uiso 1 1 calc R
C28 C -0.7469(2) 0.02640(18) -0.51328(18) 0.0379(5) Uani 1 1 d .
H28A H -0.6848 -0.0179 -0.5621 0.045 Uiso 1 1 calc R
H28B H -0.8217 0.0442 -0.5629 0.045 Uiso 1 1 calc R
C29 C -0.8205(2) -0.04593(19) -0.46145(18) 0.0408(6) Uani 1 1 d .
H29A H -0.8736 0.0014 -0.4056 0.049 Uiso 1 1 calc R
H29B H -0.8912 -0.1146 -0.5241 0.049 Uiso 1 1 calc R
C30 C -0.7625(2) -0.14180(18) -0.33961(18) 0.0385(6) Uani 1 1 d .
H30A H -0.8274 -0.2175 -0.3947 0.046 Uiso 1 1 calc R
H30B H -0.8188 -0.0940 -0.2871 0.046 Uiso 1 1 calc R
C31 C -0.6318(2) -0.16084(16) -0.26881(17) 0.0341(5) Uani 1 1 d .
H31A H -0.6652 -0.2088 -0.2312 0.041 Uiso 1 1 calc R
H31B H -0.5704 -0.2022 -0.3204 0.041 Uiso 1 1 calc R
C32 C -0.4079(2) -0.05300(15) -0.12154(17) 0.0255(5) Uani 1 1 d .
H32A H -0.3612 -0.1073 -0.1781 0.031 Uiso 1 1 calc R
H32B H -0.4202 -0.0812 -0.0628 0.031 Uiso 1 1 calc R
C41 C 0.4406(7) 0.4435(5) 0.4369(5) 0.0713(17) Uani 0.50 1 d P
H41A H 0.4121 0.3593 0.4142 0.086 Uiso 0.50 1 calc PR
H41B H 0.3823 0.4605 0.3773 0.086 Uiso 0.50 1 calc PR
Cl2 Cl 0.4057(6) 0.5274(4) 0.5776(5) 0.1007(16) Uani 0.50 1 d P
Cl3 Cl 0.6255(6) 0.4794(5) 0.4444(6) 0.134(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'
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 119.76(7) . .
C21 Sn1 C7 123.21(7) . .
C1 Sn1 C7 112.33(7) . .
C21 Sn1 Cl1 96.53(5) . .
C1 Sn1 Cl1 97.15(5) . .
C7 Sn1 Cl1 98.05(5) . .
C21 Sn1 O1 72.75(5) . .
C1 Sn1 O1 87.98(6) . .
C7 Sn1 O1 88.63(6) . .
Cl1 Sn1 O1 169.26(3) . .
C24 O1 C23 114.41(13) . .
C24 O1 Sn1 124.32(10) . .
C23 O1 Sn1 108.96(9) . .
C25 O2 C26 112.26(14) . .
C27 O3 C28 111.71(15) . .
C30 O4 C29 113.65(15) . .
C31 O5 C32 113.68(14) . .
C2 C1 C6 117.74(17) . .
C2 C1 Sn1 118.74(14) . .
C6 C1 Sn1 123.48(13) . .
C1 C2 C3 121.08(19) . .
C4 C3 C2 120.4(2) . .
C3 C4 C5 119.71(19) . .
C4 C5 C6 119.67(19) . .
C5 C6 C1 121.40(18) . .
C12 C7 C8 117.53(18) . .
C12 C7 Sn1 120.36(15) . .
C8 C7 Sn1 122.02(14) . .
C7 C8 C9 121.5(2) . .
C10 C9 C8 120.2(2) . .
C9 C10 C11 119.4(2) . .
C10 C11 C12 120.4(2) . .
C7 C12 C11 121.1(2) . .
C22 C21 Sn1 114.26(12) . .
C23 C22 C32 110.11(15) . .
C23 C22 C21 111.06(15) . .
C32 C22 C21 109.87(14) . .
O1 C23 C22 106.87(14) . .
O1 C24 C25 114.39(15) . .
O2 C25 C24 109.90(15) . .
O2 C26 C27 109.52(17) . .
O3 C27 C26 109.48(17) . .
O3 C28 C29 108.62(16) . .
O4 C29 C28 108.23(17) . .
O4 C30 C31 108.06(16) . .
O5 C31 C30 108.28(16) . .
O5 C32 C22 108.62(14) . .
Cl3 C41 Cl2 109.2(4) . .
Cl3 Cl2 C41 122.6(19) 2_666 2_666
Cl3 Cl2 C41 70.2(19) 2_666 .
C41 Cl2 C41 63.1(4) 2_666 .
Cl2 Cl3 C41 98.8(19) 2_666 2_666
Cl2 Cl3 C41 47.7(16) 2_666 .
C41 Cl3 C41 61.2(4) 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 C21 2.1307(16) .
Sn1 C1 2.1312(18) .
Sn1 C7 2.1439(18) .
Sn1 Cl1 2.4541(5) .
Sn1 O1 2.5706(12) .
O1 C24 1.4418(19) .
O1 C23 1.4562(19) .
O2 C25 1.419(2) .
O2 C26 1.423(2) .
O3 C27 1.414(2) .
O3 C28 1.414(2) .
O4 C30 1.411(2) .
O4 C29 1.414(2) .
O5 C31 1.414(2) .
O5 C32 1.422(2) .
C1 C2 1.384(3) .
C1 C6 1.395(2) .
C2 C3 1.386(3) .
C3 C4 1.374(3) .
C4 C5 1.383(3) .
C5 C6 1.385(3) .
C7 C12 1.385(3) .
C7 C8 1.386(3) .
C8 C9 1.390(3) .
C9 C10 1.371(3) .
C10 C11 1.376(3) .
C11 C12 1.392(3) .
C21 C22 1.520(2) .
C22 C23 1.518(2) .
C22 C32 1.519(2) .
C24 C25 1.495(3) .
C26 C27 1.499(3) .
C28 C29 1.500(3) .
C30 C31 1.493(3) .
C41 Cl3 1.707(8) .
C41 Cl2 1.771(9) .
Cl2 Cl3 0.342(11) 2_666
Cl2 C41 1.498(8) 2_666
Cl3 Cl2 0.342(11) 2_666
Cl3 C41 1.686(8) 2_666
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 -145.17(14) .
C1 Sn1 O1 C24 -23.10(13) .
C7 Sn1 O1 C24 89.30(13) .
Cl1 Sn1 O1 C24 -141.96(15) .
C21 Sn1 O1 C23 -5.38(10) .
C1 Sn1 O1 C23 116.69(11) .
C7 Sn1 O1 C23 -130.90(11) .
Cl1 Sn1 O1 C23 -2.2(2) .
C21 Sn1 C1 C2 -160.00(15) .
C7 Sn1 C1 C2 43.53(17) .
Cl1 Sn1 C1 C2 -58.25(16) .
O1 Sn1 C1 C2 131.22(16) .
C21 Sn1 C1 C6 17.53(18) .
C7 Sn1 C1 C6 -138.94(15) .
Cl1 Sn1 C1 C6 119.28(15) .
O1 Sn1 C1 C6 -51.26(15) .
C6 C1 C2 C3 -0.2(3) .
Sn1 C1 C2 C3 177.49(16) .
C1 C2 C3 C4 -0.1(3) .
C2 C3 C4 C5 0.2(3) .
C3 C4 C5 C6 0.0(3) .
C4 C5 C6 C1 -0.3(3) .
C2 C1 C6 C5 0.4(3) .
Sn1 C1 C6 C5 -177.17(14) .
C21 Sn1 C7 C12 110.36(15) .
C1 Sn1 C7 C12 -94.12(15) .
Cl1 Sn1 C7 C12 7.07(15) .
O1 Sn1 C7 C12 178.63(15) .
C21 Sn1 C7 C8 -73.11(16) .
C1 Sn1 C7 C8 82.42(16) .
Cl1 Sn1 C7 C8 -176.40(14) .
O1 Sn1 C7 C8 -4.84(15) .
C12 C7 C8 C9 -0.2(3) .
Sn1 C7 C8 C9 -176.85(14) .
C7 C8 C9 C10 0.0(3) .
C8 C9 C10 C11 0.0(3) .
C9 C10 C11 C12 0.1(3) .
C8 C7 C12 C11 0.3(3) .
Sn1 C7 C12 C11 177.00(15) .
C10 C11 C12 C7 -0.2(3) .
C1 Sn1 C21 C22 -101.42(14) .
C7 Sn1 C21 C22 52.38(16) .
Cl1 Sn1 C21 C22 156.47(12) .
O1 Sn1 C21 C22 -24.13(12) .
Sn1 C21 C22 C23 53.55(17) .
Sn1 C21 C22 C32 175.62(12) .
C24 O1 C23 C22 176.41(14) .
Sn1 O1 C23 C22 32.25(15) .
C32 C22 C23 O1 -177.39(14) .
C21 C22 C23 O1 -55.46(19) .
C23 O1 C24 C25 81.69(19) .
Sn1 O1 C24 C25 -140.41(13) .
C26 O2 C25 C24 -176.88(16) .
O1 C24 C25 O2 -73.6(2) .
C25 O2 C26 C27 173.02(16) .
C28 O3 C27 C26 -168.43(17) .
O2 C26 C27 O3 69.0(2) .
C27 O3 C28 C29 169.08(17) .
C30 O4 C29 C28 173.86(16) .
O3 C28 C29 O4 -67.1(2) .
C29 O4 C30 C31 -172.27(16) .
C32 O5 C31 C30 -169.61(15) .
O4 C30 C31 O5 65.9(2) .
C31 O5 C32 C22 161.96(15) .
C23 C22 C32 O5 -66.44(19) .
C21 C22 C32 O5 170.93(14) .
Cl3 C41 Cl2 Cl3 152.0(13) 2_666
Cl3 C41 Cl2 C41 6.5(3) 2_666
Cl2 C41 Cl3 Cl2 -143.4(18) 2_666
Cl2 C41 Cl3 C41 -5.9(3) 2_666
