#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:38:05 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179070 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/32/4303299.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_4303299
loop_
_publ_author_name
'Anukul Jana'
'Herbert W. Roesky'
'Carola Schulzke'
_publ_section_title
;
Hydrostannylation of Ketones and Alkynes with LSnH [L = HC(CMeNAr)2, Ar =
2,6-iPr2C6H3]
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9543
_journal_page_last               9548
_journal_paper_doi               10.1021/ic9012069
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C33 H46 N2 O2 Sn'
_chemical_formula_weight         621.41
_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                115.84(3)
_cell_angle_beta                 93.10(3)
_cell_angle_gamma                108.12(3)
_cell_formula_units_Z            2
_cell_length_a                   11.067(2)
_cell_length_b                   12.259(3)
_cell_length_c                   13.922(3)
_cell_measurement_reflns_used    14660
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      54.1
_cell_measurement_theta_min      3.3
_cell_volume                     1575.4(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  IPDSII
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14660
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.9407
_exptl_absorpt_correction_T_min  0.8350
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.493
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0317
_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)+(0.0275P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0576
_reflns_number_gt                5889
_reflns_number_total             6731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9012069_si_001_3.cif
_cod_data_source_block           ja36
_cod_original_cell_volume        1575.4(6)
_cod_database_code               4303299
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.344321(15) 0.047278(15) 0.804814(14) 0.01607(5) Uani 1 1 d . . .
O1 O 0.63039(17) 0.1214(2) 0.90269(15) 0.0414(5) Uani 1 1 d . . .
O2 O 0.73353(17) 0.04165(19) 0.77035(16) 0.0379(5) Uani 1 1 d . . .
N1 N 0.19979(17) -0.13642(17) 0.67241(15) 0.0187(4) Uani 1 1 d . . .
N2 N 0.29726(17) 0.13947(16) 0.70940(15) 0.0177(4) Uani 1 1 d . . .
C1 C 0.5099(2) 0.0190(2) 0.7240(2) 0.0217(5) Uani 1 1 d . . .
C2 C 0.5085(2) -0.0292(2) 0.6185(2) 0.0286(5) Uani 1 1 d . . .
H2A H 0.5853 -0.0362 0.5935 0.036(6) Uiso 1 1 calc R . .
H2B H 0.4306 -0.0569 0.5675 0.036(6) Uiso 1 1 calc R . .
C3 C 0.6365(2) 0.0595(2) 0.7969(2) 0.0269(5) Uani 1 1 d . . .
C4 C 0.7461(3) 0.1635(5) 0.9823(3) 0.0721(13) Uani 1 1 d . . .
H4A H 0.7644 0.0872 0.9747 0.0588(18) Uiso 1 1 calc R . .
H4B H 0.7328 0.2103 1.0560 0.0588(18) Uiso 1 1 calc R . .
H4C H 0.8200 0.2216 0.9702 0.0588(18) Uiso 1 1 calc R . .
C5 C 0.1420(2) -0.2375(2) 0.70195(18) 0.0201(5) Uani 1 1 d . . .
C6 C 0.2092(2) -0.3169(2) 0.70552(19) 0.0229(5) Uani 1 1 d . . .
C7 C 0.1521(2) -0.4092(2) 0.7395(2) 0.0273(5) Uani 1 1 d . . .
H7 H 0.1961 -0.4633 0.7427 0.030(3) Uiso 1 1 calc R . .
C8 C 0.0329(2) -0.4232(2) 0.7686(2) 0.0286(5) Uani 1 1 d . . .
H8 H -0.0043 -0.4863 0.7915 0.030(3) Uiso 1 1 calc R . .
C9 C -0.0322(2) -0.3452(2) 0.7642(2) 0.0277(5) Uani 1 1 d . . .
H9 H -0.1142 -0.3558 0.7840 0.030(3) Uiso 1 1 calc R . .
C10 C 0.0203(2) -0.2513(2) 0.73134(19) 0.0223(5) Uani 1 1 d . . .
C11 C 0.3414(3) -0.3029(2) 0.6763(2) 0.0289(5) Uani 1 1 d . . .
H11 H 0.3569 -0.2480 0.6388 0.022(3) Uiso 1 1 calc R . .
C12 C 0.3468(4) -0.4352(3) 0.5977(3) 0.0507(9) Uani 1 1 d . . .
H12A H 0.3347 -0.4899 0.6336 0.0588(18) Uiso 1 1 calc R . .
H12B H 0.4317 -0.4216 0.5776 0.0588(18) Uiso 1 1 calc R . .
H12C H 0.2775 -0.4786 0.5317 0.0588(18) Uiso 1 1 calc R . .
C13 C 0.4501(3) -0.2327(3) 0.7800(3) 0.0391(7) Uani 1 1 d . . .
H13A H 0.4463 -0.1478 0.8290 0.0588(18) Uiso 1 1 calc R . .
H13B H 0.5350 -0.2194 0.7598 0.0588(18) Uiso 1 1 calc R . .
H13C H 0.4384 -0.2859 0.8172 0.0588(18) Uiso 1 1 calc R . .
C14 C -0.0520(2) -0.1628(2) 0.7342(2) 0.0247(5) Uani 1 1 d . . .
H14 H -0.0086 -0.1120 0.6975 0.022(3) Uiso 1 1 calc R . .
C15 C -0.0406(3) -0.0662(3) 0.8530(2) 0.0359(6) Uani 1 1 d . . .
H15A H -0.0845 -0.1138 0.8902 0.0588(18) Uiso 1 1 calc R . .
H15B H -0.0817 -0.0052 0.8549 0.0588(18) Uiso 1 1 calc R . .
H15C H 0.0516 -0.0175 0.8901 0.0588(18) Uiso 1 1 calc R . .
C16 C -0.1954(3) -0.2379(3) 0.6751(2) 0.0381(7) Uani 1 1 d . . .
H16A H -0.2020 -0.2995 0.5989 0.0588(18) Uiso 1 1 calc R . .
H16B H -0.2356 -0.1763 0.6769 0.0588(18) Uiso 1 1 calc R . .
H16C H -0.2408 -0.2859 0.7115 0.0588(18) Uiso 1 1 calc R . .
C17 C 0.1570(2) -0.1567(2) 0.57219(18) 0.0203(5) Uani 1 1 d . . .
C18 C 0.0732(2) -0.2947(2) 0.4855(2) 0.0290(6) Uani 1 1 d . . .
H18A H 0.1146 -0.3548 0.4850 0.0588(18) Uiso 1 1 calc R . .
H18B H 0.0639 -0.2985 0.4136 0.0588(18) Uiso 1 1 calc R . .
H18C H -0.0131 -0.3198 0.5019 0.0588(18) Uiso 1 1 calc R . .
C19 C 0.1802(2) -0.0597(2) 0.54118(18) 0.0209(5) Uani 1 1 d . . .
H19 H 0.1561 -0.0907 0.4647 0.030(3) Uiso 1 1 calc R . .
C20 C 0.2341(2) 0.0781(2) 0.60579(19) 0.0196(5) Uani 1 1 d . . .
C21 C 0.2127(2) 0.1535(2) 0.5497(2) 0.0281(5) Uani 1 1 d . . .
H21A H 0.2346 0.2449 0.6043 0.0588(18) Uiso 1 1 calc R . .
H21B H 0.1211 0.1156 0.5115 0.0588(18) Uiso 1 1 calc R . .
H21C H 0.2684 0.1490 0.4968 0.0588(18) Uiso 1 1 calc R . .
C22 C 0.3437(2) 0.2804(2) 0.77335(18) 0.0186(4) Uani 1 1 d . . .
C23 C 0.4634(2) 0.3592(2) 0.76785(19) 0.0216(5) Uani 1 1 d . . .
C24 C 0.5075(2) 0.4941(2) 0.8367(2) 0.0260(5) Uani 1 1 d . . .
H24 H 0.5877 0.5488 0.8332 0.030(3) Uiso 1 1 calc R . .
C25 C 0.4375(2) 0.5499(2) 0.9099(2) 0.0274(5) Uani 1 1 d . . .
H25 H 0.4701 0.6416 0.9567 0.030(3) Uiso 1 1 calc R . .
C26 C 0.3200(2) 0.4712(2) 0.9143(2) 0.0246(5) Uani 1 1 d . . .
H26 H 0.2714 0.5099 0.9638 0.030(3) Uiso 1 1 calc R . .
C27 C 0.2707(2) 0.3357(2) 0.84733(19) 0.0211(5) Uani 1 1 d . . .
C28 C 0.5480(2) 0.3045(2) 0.6923(2) 0.0270(5) Uani 1 1 d . . .
H28 H 0.5007 0.2079 0.6483 0.022(3) Uiso 1 1 calc R . .
C29 C 0.5715(3) 0.3594(3) 0.6124(2) 0.0393(7) Uani 1 1 d . . .
H29A H 0.4876 0.3415 0.5699 0.0588(18) Uiso 1 1 calc R . .
H29B H 0.6220 0.3180 0.5627 0.0588(18) Uiso 1 1 calc R . .
H29C H 0.6201 0.4539 0.6533 0.0588(18) Uiso 1 1 calc R . .
C30 C 0.6781(2) 0.3293(3) 0.7584(3) 0.0373(7) Uani 1 1 d . . .
H30A H 0.7310 0.4230 0.7957 0.0588(18) Uiso 1 1 calc R . .
H30B H 0.7249 0.2816 0.7089 0.0588(18) Uiso 1 1 calc R . .
H30C H 0.6615 0.2992 0.8128 0.0588(18) Uiso 1 1 calc R . .
C31 C 0.1396(2) 0.2529(2) 0.8534(2) 0.0242(5) Uani 1 1 d . . .
H31 H 0.1315 0.1597 0.8145 0.022(3) Uiso 1 1 calc R . .
C32 C 0.0287(3) 0.2648(4) 0.7946(4) 0.0675(12) Uani 1 1 d . . .
H32A H 0.0334 0.3552 0.8316 0.0588(18) Uiso 1 1 calc R . .
H32B H -0.0548 0.2068 0.7955 0.0588(18) Uiso 1 1 calc R . .
H32C H 0.0359 0.2400 0.7187 0.0588(18) Uiso 1 1 calc R . .
C33 C 0.1282(3) 0.2863(3) 0.9706(2) 0.0464(8) Uani 1 1 d . . .
H33A H 0.1302 0.3757 1.0095 0.0588(18) Uiso 1 1 calc R . .
H33B H 0.2012 0.2795 1.0075 0.0588(18) Uiso 1 1 calc R . .
H33C H 0.0458 0.2254 0.9700 0.0588(18) 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'
N N 0.0061 0.0033 '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
N1 Sn1 N2 85.64(7) . . ?
N1 Sn1 C1 93.06(8) . . ?
N2 Sn1 C1 91.14(8) . . ?
C3 O1 C4 116.0(2) . . ?
C17 N1 C5 119.14(18) . . ?
C17 N1 Sn1 125.22(15) . . ?
C5 N1 Sn1 115.48(14) . . ?
C20 N2 C22 121.3(2) . . ?
C20 N2 Sn1 126.31(15) . . ?
C22 N2 Sn1 112.43(14) . . ?
C2 C1 C3 115.8(2) . . ?
C2 C1 Sn1 127.40(18) . . ?
C3 C1 Sn1 116.79(17) . . ?
O2 C3 O1 122.1(2) . . ?
O2 C3 C1 127.6(2) . . ?
O1 C3 C1 110.2(2) . . ?
C6 C5 C10 120.9(2) . . ?
C6 C5 N1 120.3(2) . . ?
C10 C5 N1 118.7(2) . . ?
C7 C6 C5 118.2(2) . . ?
C7 C6 C11 119.6(2) . . ?
C5 C6 C11 122.2(2) . . ?
C8 C7 C6 121.2(2) . . ?
C9 C8 C7 119.9(2) . . ?
C8 C9 C10 121.3(2) . . ?
C9 C10 C5 118.4(2) . . ?
C9 C10 C14 119.0(2) . . ?
C5 C10 C14 122.5(2) . . ?
C6 C11 C12 112.0(2) . . ?
C6 C11 C13 110.7(2) . . ?
C12 C11 C13 110.3(2) . . ?
C10 C14 C15 109.4(2) . . ?
C10 C14 C16 113.2(2) . . ?
C15 C14 C16 110.0(2) . . ?
N1 C17 C19 124.9(2) . . ?
N1 C17 C18 118.4(2) . . ?
C19 C17 C18 116.7(2) . . ?
C17 C19 C20 130.1(2) . . ?
N2 C20 C19 123.7(2) . . ?
N2 C20 C21 120.8(2) . . ?
C19 C20 C21 115.5(2) . . ?
C23 C22 C27 120.92(19) . . ?
C23 C22 N2 120.6(2) . . ?
C27 C22 N2 118.28(19) . . ?
C24 C23 C22 118.2(2) . . ?
C24 C23 C28 118.7(2) . . ?
C22 C23 C28 123.1(2) . . ?
C25 C24 C23 121.7(2) . . ?
C26 C25 C24 119.5(2) . . ?
C25 C26 C27 121.4(2) . . ?
C26 C27 C22 118.3(2) . . ?
C26 C27 C31 119.7(2) . . ?
C22 C27 C31 121.97(19) . . ?
C23 C28 C29 112.2(2) . . ?
C23 C28 C30 110.8(2) . . ?
C29 C28 C30 110.5(2) . . ?
C32 C31 C33 110.6(3) . . ?
C32 C31 C27 110.7(2) . . ?
C33 C31 C27 112.5(2) . . ?
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 N1 2.202(2) . ?
Sn1 N2 2.217(2) . ?
Sn1 C1 2.241(2) . ?
O1 C3 1.348(3) . ?
O1 C4 1.439(3) . ?
O2 C3 1.207(3) . ?
N1 C17 1.336(3) . ?
N1 C5 1.447(3) . ?
N2 C20 1.324(3) . ?
N2 C22 1.449(3) . ?
C1 C2 1.320(4) . ?
C1 C3 1.488(3) . ?
C5 C6 1.410(3) . ?
C5 C10 1.411(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.518(3) . ?
C7 C8 1.383(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.394(3) . ?
C10 C14 1.524(3) . ?
C11 C12 1.534(4) . ?
C11 C13 1.534(4) . ?
C14 C15 1.526(4) . ?
C14 C16 1.528(3) . ?
C17 C19 1.392(3) . ?
C17 C18 1.517(3) . ?
C19 C20 1.417(3) . ?
C20 C21 1.505(3) . ?
C22 C23 1.404(3) . ?
C22 C27 1.413(3) . ?
C23 C24 1.399(3) . ?
C23 C28 1.521(3) . ?
C24 C25 1.383(4) . ?
C25 C26 1.381(4) . ?
C26 C27 1.399(3) . ?
C27 C31 1.522(3) . ?
C28 C29 1.527(4) . ?
C28 C30 1.534(4) . ?
C31 C32 1.518(4) . ?
C31 C33 1.521(4) . ?
