#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:03:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178735 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/46/4084617.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_4084617
loop_
_publ_author_name
'Chlupatý, Tomáš'
'R°užičková, Zdeňka'
'Horáček, Michal'
'Merna, Jan'
'Alonso, Mercedes'
'De Proft, Frank'
'R°užička, Aleš'
_publ_section_title
;
 Reactivity of Tin(II) Guanidinate with 1,2- and 1,3-Diones: Oxidative
 Cycloaddition or Ligand Substitution ?
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2202
_journal_paper_doi               10.1021/om500873a
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C42 H64 Cl2 N6 Si4 Sn, C4 H10 O'
_chemical_formula_sum            'C46 H74 Cl2 N6 O Si4 Sn'
_chemical_formula_weight         1029.06
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4670(11)
_cell_length_b                   17.8150(11)
_cell_length_c                   18.3959(15)
_cell_measurement_reflns_used    21679
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     5396.6(7)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21641
_diffrn_reflns_theta_full        27.25
_diffrn_reflns_theta_max         27.25
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0449
_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)+(0.0090P)²+11.2656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                3994
_reflns_number_total             5971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500873a_si_001.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 4084614--4084619.cif.'
_cod_database_code               4084617
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, 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 0.7500 0.120955(18) 0.01979(8) Uani 1 2 d S
Si2 Si -0.02670(6) 0.82641(6) 0.02028(6) 0.0264(2) Uani 1 1 d .
Si1 Si 0.01352(6) 0.66813(6) -0.04380(6) 0.0268(2) Uani 1 1 d .
Cl1 Cl 0.29786(6) 0.66255(6) 0.20904(5) 0.0397(3) Uani 1 1 d .
N2 N 0.17085(17) 0.80041(16) 0.03906(15) 0.0213(6) Uani 1 1 d .
N1 N 0.13887(16) 0.69489(16) 0.09340(15) 0.0218(6) Uani 1 1 d .
N3 N 0.03951(15) 0.74766(18) 0.01051(14) 0.0227(6) Uani 1 1 d .
C1 C 0.11390(18) 0.7484(2) 0.04581(16) 0.0212(6) Uani 1 1 d .
C2 C 0.0861(2) 0.64714(18) 0.13308(19) 0.0228(7) Uani 1 1 d .
C10 C 0.1923(2) 0.9297(2) 0.0056(2) 0.0250(8) Uani 1 1 d .
H10 H 0.1971 0.9414 0.0547 0.030 Uiso 1 1 d R
C9 C 0.1758(2) 0.85595(19) -0.01594(19) 0.0227(7) Uani 1 1 d .
C4 C -0.0298(2) 0.6265(2) 0.2092(2) 0.0363(10) Uani 1 1 d .
H4 H -0.0741 0.6460 0.2342 0.044 Uiso 1 1 d R
C19 C 0.0017(2) 0.8797(2) 0.1029(2) 0.0352(9) Uani 1 1 d .
H19A H -0.0056 0.8487 0.1450 0.042 Uiso 1 1 d R
H19B H -0.0320 0.9234 0.1068 0.042 Uiso 1 1 d R
H19C H 0.0576 0.8947 0.0995 0.042 Uiso 1 1 d R
C18 C -0.0302(2) 0.7061(2) -0.1298(2) 0.0332(9) Uani 1 1 d .
H18A H -0.0814 0.7298 -0.1197 0.040 Uiso 1 1 d R
H18B H -0.0383 0.6659 -0.1637 0.040 Uiso 1 1 d R
H18C H 0.0065 0.7423 -0.1503 0.040 Uiso 1 1 d R
C7 C 0.1037(2) 0.5710(2) 0.1376(2) 0.0272(8) Uani 1 1 d .
H7 H 0.1493 0.5521 0.1141 0.033 Uiso 1 1 d R
C17 C -0.0608(2) 0.6043(2) 0.0008(2) 0.0342(9) Uani 1 1 d .
H17A H -0.0397 0.5881 0.0468 0.041 Uiso 1 1 d R
H17B H -0.0701 0.5615 -0.0298 0.041 Uiso 1 1 d R
H17C H -0.1110 0.6306 0.0082 0.041 Uiso 1 1 d R
C6 C 0.0537(2) 0.5233(2) 0.1768(2) 0.0304(9) Uani 1 1 d .
H6 H 0.0663 0.4725 0.1793 0.037 Uiso 1 1 d R
C20 C -0.1313(2) 0.7885(2) 0.0333(2) 0.0340(9) Uani 1 1 d .
H20A H -0.1493 0.7653 -0.0110 0.041 Uiso 1 1 d R
H20B H -0.1675 0.8286 0.0459 0.041 Uiso 1 1 d R
H20C H -0.1309 0.7519 0.0716 0.041 Uiso 1 1 d R
C21 C -0.0268(2) 0.8930(2) -0.0577(2) 0.0341(9) Uani 1 1 d .
H21A H 0.0260 0.9154 -0.0624 0.041 Uiso 1 1 d R
H21B H -0.0664 0.9316 -0.0494 0.041 Uiso 1 1 d R
H21C H -0.0400 0.8664 -0.1015 0.041 Uiso 1 1 d R
C11 C 0.2013(2) 0.9852(2) -0.0464(2) 0.0334(9) Uani 1 1 d .
H11 H 0.2131 1.0340 -0.0317 0.040 Uiso 1 1 d R
C5 C -0.0146(2) 0.5496(2) 0.2121(2) 0.0304(9) Uani 1 1 d .
C3 C 0.0198(2) 0.6745(2) 0.1707(2) 0.0311(9) Uani 1 1 d .
H3 H 0.0082 0.7255 0.1696 0.037 Uiso 1 1 d R
C14 C 0.1691(2) 0.8397(2) -0.08935(19) 0.0289(8) Uani 1 1 d .
H14 H 0.1597 0.7907 -0.1045 0.035 Uiso 1 1 d R
C16 C 0.1066(2) 0.6150(2) -0.0661(2) 0.0366(10) Uani 1 1 d .
H16A H 0.1445 0.6474 -0.0902 0.044 Uiso 1 1 d R
H16B H 0.0933 0.5737 -0.0973 0.044 Uiso 1 1 d R
H16C H 0.1303 0.5964 -0.0220 0.044 Uiso 1 1 d R
O28 O 0.2500 0.2500 0.1429(2) 0.0487(10) Uani 1 2 d S
C12 C 0.1937(2) 0.9700(2) -0.1203(2) 0.0342(9) Uani 1 1 d .
C15 C 0.2046(3) 1.0308(3) -0.1766(2) 0.0531(13) Uani 1 1 d .
H15A H 0.2168 1.0082 -0.2227 0.064 Uiso 1 1 d R
H15B H 0.2485 1.0631 -0.1625 0.064 Uiso 1 1 d R
H15C H 0.1555 1.0596 -0.1806 0.064 Uiso 1 1 d R
C13 C 0.1768(2) 0.8965(2) -0.1402(2) 0.0346(10) Uani 1 1 d .
H13 H 0.1703 0.8852 -0.1892 0.042 Uiso 1 1 d R
C8 C -0.0702(3) 0.4973(3) 0.2528(2) 0.0459(11) Uani 1 1 d .
H8A H -0.0764 0.5147 0.3019 0.055 Uiso 1 1 d R
H8B H -0.0473 0.4477 0.2531 0.055 Uiso 1 1 d R
H8C H -0.1224 0.4960 0.2295 0.055 Uiso 1 1 d R
C22 C 0.2503(3) 0.1835(3) 0.1856(2) 0.0627(14) Uani 1 1 d .
H22A H 0.2029 0.1824 0.2168 0.075 Uiso 1 1 d R
H22B H 0.2984 0.1826 0.2162 0.075 Uiso 1 1 d R
C23 C 0.2503(3) 0.1165(3) 0.1362(3) 0.0598(13) Uani 1 1 d .
H23A H 0.2042 0.1190 0.1045 0.072 Uiso 1 1 d R
H23B H 0.2474 0.0715 0.1649 0.072 Uiso 1 1 d R
H23C H 0.2992 0.1160 0.1078 0.072 Uiso 1 1 d 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.026
-1 -1 0 0.097
-1 1 0 0.055
1 -1 0 0.107
0 0 -1 0.035
0 0 1 0.131
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
N1 Sn1 N1 152.57(15) . 2_565
N1 Sn1 N2 60.97(10) . .
N1 Sn1 N2 99.11(10) 2_565 .
N1 Sn1 N2 99.11(10) . 2_565
N1 Sn1 N2 60.97(10) 2_565 2_565
N2 Sn1 N2 92.83(15) . 2_565
N1 Sn1 Cl1 100.28(8) . 2_565
N1 Sn1 Cl1 98.29(8) 2_565 2_565
N2 Sn1 Cl1 90.16(8) . 2_565
N2 Sn1 Cl1 159.25(8) 2_565 2_565
N1 Sn1 Cl1 98.29(8) . .
N1 Sn1 Cl1 100.28(8) 2_565 .
N2 Sn1 Cl1 159.25(8) . .
N2 Sn1 Cl1 90.16(8) 2_565 .
Cl1 Sn1 Cl1 94.27(6) 2_565 .
N1 Sn1 C1 30.91(11) . .
N1 Sn1 C1 127.52(11) 2_565 .
N2 Sn1 C1 30.10(11) . .
N2 Sn1 C1 98.12(10) 2_565 .
Cl1 Sn1 C1 94.74(8) 2_565 .
Cl1 Sn1 C1 129.17(9) . .
N1 Sn1 C1 127.52(11) . 2_565
N1 Sn1 C1 30.91(11) 2_565 2_565
N2 Sn1 C1 98.12(10) . 2_565
N2 Sn1 C1 30.11(11) 2_565 2_565
Cl1 Sn1 C1 129.17(9) 2_565 2_565
Cl1 Sn1 C1 94.74(8) . 2_565
C1 Sn1 C1 116.67(13) . 2_565
N3 Si2 C19 109.32(15) . .
N3 Si2 C21 115.08(16) . .
C19 Si2 C21 107.80(18) . .
N3 Si2 C20 106.96(16) . .
C19 Si2 C20 108.29(19) . .
C21 Si2 C20 109.22(18) . .
N3 Si1 C16 109.36(16) . .
N3 Si1 C17 113.31(16) . .
C16 Si1 C17 109.32(19) . .
N3 Si1 C18 106.22(15) . .
C16 Si1 C18 108.55(19) . .
C17 Si1 C18 109.95(17) . .
C1 N2 C9 126.6(3) . .
C1 N2 Sn1 94.0(2) . .
C9 N2 Sn1 138.1(2) . .
C1 N1 C2 124.6(3) . .
C1 N1 Sn1 95.1(2) . .
C2 N1 Sn1 132.7(2) . .
C1 N3 Si1 118.8(2) . .
C1 N3 Si2 119.0(2) . .
Si1 N3 Si2 122.23(15) . .
N2 C1 N1 109.7(3) . .
N2 C1 N3 126.1(3) . .
N1 C1 N3 124.2(3) . .
N2 C1 Sn1 55.87(16) . .
N1 C1 Sn1 53.95(16) . .
N3 C1 Sn1 176.3(2) . .
C3 C2 C7 118.6(3) . .
C3 C2 N1 122.1(3) . .
C7 C2 N1 119.3(3) . .
C11 C10 C9 119.7(3) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.2 . .
C14 C9 C10 119.2(3) . .
C14 C9 N2 123.1(3) . .
C10 C9 N2 117.7(3) . .
C3 C4 C5 121.5(4) . .
C3 C4 H4 119.2 . .
C5 C4 H4 119.3 . .
Si2 C19 H19A 109.6 . .
Si2 C19 H19B 109.4 . .
H19A C19 H19B 109.5 . .
Si2 C19 H19C 109.4 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
Si1 C18 H18A 109.5 . .
Si1 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
Si1 C18 H18C 109.4 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C6 C7 C2 120.4(3) . .
C6 C7 H7 119.9 . .
C2 C7 H7 119.7 . .
Si1 C17 H17A 109.6 . .
Si1 C17 H17B 109.4 . .
H17A C17 H17B 109.5 . .
Si1 C17 H17C 109.4 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C5 C6 C7 121.4(4) . .
C5 C6 H6 119.3 . .
C7 C6 H6 119.3 . .
Si2 C20 H20A 109.4 . .
Si2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
Si2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
Si2 C21 H21A 109.5 . .
Si2 C21 H21B 109.6 . .
H21A C21 H21B 109.5 . .
Si2 C21 H21C 109.4 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C10 C11 C12 121.7(4) . .
C10 C11 H11 119.2 . .
C12 C11 H11 119.1 . .
C6 C5 C4 117.5(4) . .
C6 C5 C8 121.4(4) . .
C4 C5 C8 121.2(4) . .
C4 C3 C2 120.5(4) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.7 . .
C13 C14 C9 120.0(4) . .
C13 C14 H14 120.0 . .
C9 C14 H14 120.1 . .
Si1 C16 H16A 109.6 . .
Si1 C16 H16B 109.7 . .
H16A C16 H16B 109.5 . .
Si1 C16 H16C 109.2 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C22 O28 C22 112.9(5) 2 .
C13 C12 C11 117.4(3) . .
C13 C12 C15 121.3(4) . .
C11 C12 C15 121.3(4) . .
C12 C15 H15A 109.3 . .
C12 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C12 C15 H15C 109.6 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C13 C12 122.0(4) . .
C14 C13 H13 119.2 . .
C12 C13 H13 118.8 . .
C5 C8 H8A 109.4 . .
C5 C8 H8B 109.4 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.7 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O28 C22 C23 109.2(3) . .
O28 C22 H22A 109.9 . .
C23 C22 H22A 110.1 . .
O28 C22 H22B 109.7 . .
C23 C22 H22B 109.8 . .
H22A C22 H22B 108.3 . .
C22 C23 H23A 109.4 . .
C22 C23 H23B 109.3 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.7 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 N1 2.138(3) .
Sn1 N1 2.138(3) 2_565
Sn1 N2 2.185(3) .
Sn1 N2 2.185(3) 2_565
Sn1 Cl1 2.3819(10) 2_565
Sn1 Cl1 2.3820(10) .
Sn1 C1 2.633(3) .
Sn1 C1 2.633(3) 2_565
Si2 N3 1.786(3) .
Si2 C19 1.852(4) .
Si2 C21 1.862(4) .
Si2 C20 1.865(4) .
Si1 N3 1.786(3) .
Si1 C16 1.846(4) .
Si1 C17 1.860(4) .
Si1 C18 1.866(4) .
N2 C1 1.324(4) .
N2 C9 1.418(4) .
N1 C1 1.358(4) .
N1 C2 1.418(4) .
N3 C1 1.387(4) .
C2 C3 1.382(5) .
C2 C7 1.389(5) .
C10 C11 1.385(5) .
C10 C9 1.399(5) .
C10 H10 0.9300 .
C9 C14 1.385(5) .
C4 C3 1.378(5) .
C4 C5 1.394(6) .
C4 H4 0.9300 .
C19 H19A 0.9600 .
C19 H19B 0.9599 .
C19 H19C 0.9600 .
C18 H18A 0.9599 .
C18 H18B 0.9600 .
C18 H18C 0.9601 .
C7 C6 1.387(5) .
C7 H7 0.9301 .
C17 H17A 0.9600 .
C17 H17B 0.9601 .
C17 H17C 0.9600 .
C6 C5 1.379(5) .
C6 H6 0.9300 .
C20 H20A 0.9601 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9601 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C11 C12 1.391(6) .
C11 H11 0.9300 .
C5 C8 1.507(5) .
C3 H3 0.9298 .
C14 C13 1.383(5) .
C14 H14 0.9301 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9602 .
O28 C22 1.422(5) 2
O28 C22 1.422(5) .
C12 C13 1.388(6) .
C12 C15 1.510(5) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9602 .
C13 H13 0.9300 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C22 C23 1.500(6) .
C22 H22A 0.9699 .
C22 H22B 0.9700 .
C23 H23A 0.9601 .
C23 H23B 0.9598 .
C23 H23C 0.9599 .
