#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:03:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178800 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/54/4105413.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_4105413
loop_
_publ_author_name
'Christian Unkelbach'
'Carsten Strohmann'
_publ_contact_author_address
;
Anorganische Chemie
Technische Universität Dortmund
Otto-Hahn-Strasse
44227 Dortmund
Germany
;
_publ_contact_author_email       mail@carsten-strohmann.de
_publ_contact_author_fax         '0049 231 755 3807'
_publ_contact_author_name        'Carsten Strohmann'
_publ_contact_author_phone       '0049 231 888 3797'
_publ_section_title
;
 Low-Temperature Addition of Organolithiums to Functionalized Vinylsilanes
 under Formation of Secondary α-Lithiated Alkylsilanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17044
_journal_page_last               17045
_journal_paper_doi               10.1021/ja9076167
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C22 H54 Li2 N4 Si2'
_chemical_formula_weight         444.75
_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_date             2009-08-20T13:55:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                96.133(6)
_cell_angle_beta                 107.600(5)
_cell_angle_gamma                90.475(9)
_cell_formula_units_Z            2
_cell_length_a                   9.562(5)
_cell_length_b                   10.587(4)
_cell_length_c                   15.491(7)
_cell_measurement_reflns_used    4348
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1.39
_cell_volume                     1484.9(12)
_computing_cell_refinement       'SAINTPLUS 6.02 (Bruker AXS, 1999)'
_computing_data_collection       'SMART 5.622 (Bruker AXS, 2001)'
_computing_data_reduction        'SAINTPLUS 6.02 (Bruker AXS, 1999)'
_computing_molecular_graphics    'Ortep-3 V1.073 (Farrugia, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX-CCD'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31117
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2.01 (Bruker AXS, 1999)'
_exptl_crystal_density_diffrn    0.995
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0407P)²+1.0960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.132
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                4348
_reflns_number_total             5244
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9076167_si_002.cif
_cod_data_source_block           cu080208
_cod_original_cell_volume        1484.8(11)
_cod_database_code               4105413
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
C1 C 0.7837(4) 0.6960(3) -0.1306(2) 0.0759(10) Uani 1 1 d .
H1A H 0.681 0.7002 -0.1675 0.114 Uiso 1 1 calc R
H1B H 0.8128 0.6075 -0.1331 0.114 Uiso 1 1 calc R
H1C H 0.8463 0.7471 -0.1546 0.114 Uiso 1 1 calc R
C2 C 0.6511(3) 0.6748(3) 0.0184(2) 0.0713(9) Uani 1 1 d .
H2A H 0.6584 0.6978 0.0827 0.107 Uiso 1 1 calc R
H2B H 0.6589 0.5827 0.0068 0.107 Uiso 1 1 calc R
H2C H 0.5563 0.6999 -0.0202 0.107 Uiso 1 1 calc R
C3 C 0.8259(3) 0.9313(3) 0.01234(18) 0.0464(6) Uani 1 1 d .
H3 H 0.754(3) 0.966(3) -0.0294(19) 0.055(8) Uiso 1 1 d .
C4 C 0.8252(3) 0.9901(3) 0.1080(2) 0.0538(7) Uani 1 1 d .
H4A H 0.881(3) 0.932(3) 0.1556(19) 0.060(8) Uiso 1 1 d .
H4B H 0.883(3) 1.074(3) 0.1285(18) 0.056(8) Uiso 1 1 d .
C5 C 0.6752(3) 1.0116(3) 0.1208(2) 0.0709(9) Uani 1 1 d .
H5A H 0.6223 1.0705 0.0789 0.106 Uiso 1 1 calc R
H5B H 0.6878 1.0478 0.1838 0.106 Uiso 1 1 calc R
H5C H 0.619 0.9303 0.1082 0.106 Uiso 1 1 calc R
C6 C 0.9757(3) 0.6954(3) 0.07169(19) 0.0543(7) Uani 1 1 d .
H6A H 0.9665 0.7056 0.134 0.065 Uiso 1 1 calc R
H6B H 0.9776 0.6032 0.0532 0.065 Uiso 1 1 calc R
C7 C 1.1641(4) 0.7036(3) -0.0039(2) 0.0719(9) Uani 1 1 d .
H7A H 1.1781 0.6123 -0.0018 0.108 Uiso 1 1 calc R
H7B H 1.2564 0.7464 -0.0019 0.108 Uiso 1 1 calc R
H7C H 1.0879 0.7173 -0.0603 0.108 Uiso 1 1 calc R
C8 C 1.2342(3) 0.7392(3) 0.1602(2) 0.0633(8) Uani 1 1 d .
H8A H 1.3315 0.755 0.1524 0.076 Uiso 1 1 calc R
H8B H 1.2286 0.6502 0.1736 0.076 Uiso 1 1 calc R
C9 C 1.2189(3) 0.8286(3) 0.2397(2) 0.0631(8) Uani 1 1 d .
H9A H 1.1252 0.8073 0.2508 0.076 Uiso 1 1 calc R
H9B H 1.2999 0.8158 0.2951 0.076 Uiso 1 1 calc R
C10 C 1.1793(4) 1.0405(3) 0.2955(2) 0.0742(9) Uani 1 1 d .
H10A H 1.0806 1.0131 0.2945 0.111 Uiso 1 1 calc R
H10B H 1.1798 1.13 0.2847 0.111 Uiso 1 1 calc R
H10C H 1.2493 1.0304 0.3551 0.111 Uiso 1 1 calc R
C11 C 1.3692(3) 1.0038(3) 0.2258(2) 0.0651(8) Uani 1 1 d .
H11A H 1.4398 0.9894 0.2842 0.098 Uiso 1 1 calc R
H11B H 1.3707 1.0946 0.2185 0.098 Uiso 1 1 calc R
H11C H 1.3959 0.9553 0.176 0.098 Uiso 1 1 calc R
C12 C 0.8890(4) 0.1432(3) 0.4400(2) 0.0835(11) Uani 1 1 d .
H12A H 0.9846 0.1778 0.4404 0.125 Uiso 1 1 calc R
H12B H 0.845 0.0876 0.3831 0.125 Uiso 1 1 calc R
H12C H 0.9021 0.0942 0.4919 0.125 Uiso 1 1 calc R
C13 C 0.5944(4) 0.1996(3) 0.4625(2) 0.0782(10) Uani 1 1 d .
H13A H 0.6196 0.1659 0.5216 0.117 Uiso 1 1 calc R
H13B H 0.5569 0.1299 0.4135 0.117 Uiso 1 1 calc R
H13C H 0.519 0.2625 0.4596 0.117 Uiso 1 1 calc R
C14 C 0.8567(3) 0.4107(3) 0.53041(18) 0.0465(6) Uani 1 1 d .
H14 H 0.908(3) 0.379(3) 0.5840(19) 0.056(8) Uiso 1 1 d .
C15 C 0.7594(4) 0.5148(3) 0.5539(2) 0.0557(7) Uani 1 1 d .
H15A H 0.812(3) 0.603(3) 0.5719(19) 0.064(9) Uiso 1 1 d .
H15B H 0.673(3) 0.525(3) 0.501(2) 0.063(8) Uiso 1 1 d .
C16 C 0.6995(4) 0.4950(4) 0.6318(2) 0.0775(10) Uani 1 1 d .
H16A H 0.6341 0.4186 0.6153 0.116 Uiso 1 1 calc R
H16B H 0.6445 0.5689 0.644 0.116 Uiso 1 1 calc R
H16C H 0.781 0.4846 0.6865 0.116 Uiso 1 1 calc R
C17 C 0.6863(3) 0.3395(3) 0.33332(19) 0.0558(7) Uani 1 1 d .
H17A H 0.6532 0.2656 0.2861 0.067 Uiso 1 1 calc R
H17B H 0.5987 0.3882 0.3341 0.067 Uiso 1 1 calc R
C18 C 0.8867(4) 0.3424(3) 0.2679(2) 0.0792(10) Uani 1 1 d .
H18A H 0.8279 0.2883 0.2135 0.119 Uiso 1 1 calc R
H18B H 0.9415 0.2889 0.3135 0.119 Uiso 1 1 calc R
H18C H 0.9556 0.397 0.2515 0.119 Uiso 1 1 calc R
C19 C 0.7091(4) 0.5050(3) 0.2387(2) 0.0705(9) Uani 1 1 d .
H19A H 0.6281 0.4549 0.1917 0.085 Uiso 1 1 calc R
H19B H 0.7765 0.5379 0.208 0.085 Uiso 1 1 calc R
C20 C 0.6470(3) 0.6151(3) 0.2831(2) 0.0705(9) Uani 1 1 d .
H20A H 0.5964 0.6698 0.2362 0.085 Uiso 1 1 calc R
H20B H 0.5731 0.5821 0.3091 0.085 Uiso 1 1 calc R
C21 C 0.8512(4) 0.7664(3) 0.3166(2) 0.0704(9) Uani 1 1 d .
H21A H 0.7889 0.8227 0.2763 0.106 Uiso 1 1 calc R
H21B H 0.8989 0.7086 0.2815 0.106 Uiso 1 1 calc R
H21C H 0.9263 0.8174 0.3656 0.106 Uiso 1 1 calc R
C22 C 0.6912(4) 0.7804(3) 0.4086(3) 0.0799(10) Uani 1 1 d .
H22A H 0.6327 0.8392 0.3688 0.12 Uiso 1 1 calc R
H22B H 0.7671 0.8287 0.4588 0.12 Uiso 1 1 calc R
H22C H 0.6273 0.7321 0.4333 0.12 Uiso 1 1 calc R
Li1 Li 1.0759(5) 0.9525(4) 0.0707(3) 0.0482(10) Uani 1 1 d .
Li2 Li 0.9024(5) 0.5358(4) 0.4304(3) 0.0503(11) Uani 1 1 d .
N1 N 1.1186(3) 0.7562(2) 0.07513(15) 0.0523(6) Uani 1 1 d .
N2 N 1.2216(3) 0.9622(2) 0.22373(15) 0.0541(6) Uani 1 1 d .
N3 N 0.7891(3) 0.4219(2) 0.30597(15) 0.0542(6) Uani 1 1 d .
N4 N 0.7609(3) 0.6923(2) 0.35591(16) 0.0573(6) Uani 1 1 d .
Si1 Si 0.80520(9) 0.76004(7) -0.00880(5) 0.0520(2) Uani 1 1 d .
Si2 Si 0.76420(9) 0.27778(7) 0.44875(5) 0.0525(2) Uani 1 1 d .
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 0 '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'
Li Li -0.0003 0.0001 '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
C4 C3 Si1 115.8(2) . .
C4 C3 Li1 118.8(2) . 2_775
Si1 C3 Li1 122.16(17) . 2_775
C4 C3 Li1 85.4(2) . .
Si1 C3 Li1 99.30(17) . .
Li1 C3 Li1 68.2(2) 2_775 .
C5 C4 C3 116.4(2) . .
N1 C6 Si1 115.60(18) . .
N1 C8 C9 111.6(2) . .
N2 C9 C8 112.6(2) . .
C15 C14 Si2 116.7(2) . .
C15 C14 Li2 115.6(2) . 2_766
Si2 C14 Li2 125.37(18) . 2_766
C15 C14 Li2 87.6(2) . .
Si2 C14 Li2 98.04(17) . .
Li2 C14 Li2 69.5(2) 2_766 .
C16 C15 C14 115.8(3) . .
N3 C17 Si2 115.61(19) . .
N3 C19 C20 111.4(2) . .
N4 C20 C19 112.5(3) . .
N1 Li1 C3 120.1(2) . 2_775
N1 Li1 C3 97.7(2) . .
C3 Li1 C3 111.8(2) 2_775 .
N1 Li1 N2 81.43(17) . .
C3 Li1 N2 112.8(2) 2_775 .
C3 Li1 N2 128.3(2) . .
N1 Li1 Li1 124.4(3) . 2_775
C3 Li1 Li1 56.39(18) 2_775 2_775
C3 Li1 Li1 55.39(18) . 2_775
N2 Li1 Li1 154.2(3) . 2_775
N3 Li2 C14 122.5(2) . 2_766
N3 Li2 C14 98.9(2) . .
C14 Li2 C14 110.5(2) 2_766 .
N3 Li2 N4 81.67(17) . .
C14 Li2 N4 111.2(2) 2_766 .
C14 Li2 N4 129.3(2) . .
N3 Li2 Li2 127.3(3) . 2_766
C14 Li2 Li2 55.78(18) 2_766 2_766
C14 Li2 Li2 54.76(18) . 2_766
N4 Li2 Li2 151.0(3) . 2_766
C8 N1 C7 109.8(2) . .
C8 N1 C6 111.7(2) . .
C7 N1 C6 110.3(2) . .
C8 N1 Li1 109.5(2) . .
C7 N1 Li1 111.2(2) . .
C6 N1 Li1 104.3(2) . .
C9 N2 C11 110.4(2) . .
C9 N2 C10 109.1(2) . .
C11 N2 C10 109.1(2) . .
C9 N2 Li1 101.58(19) . .
C11 N2 Li1 105.9(2) . .
C10 N2 Li1 120.4(2) . .
C18 N3 C19 109.8(3) . .
C18 N3 C17 109.8(2) . .
C19 N3 C17 111.5(2) . .
C18 N3 Li2 113.3(2) . .
C19 N3 Li2 109.2(2) . .
C17 N3 Li2 103.1(2) . .
C21 N4 C22 108.6(3) . .
C21 N4 C20 110.2(2) . .
C22 N4 C20 109.6(3) . .
C21 N4 Li2 108.6(2) . .
C22 N4 Li2 117.9(2) . .
C20 N4 Li2 101.5(2) . .
C3 Si1 C1 113.56(14) . .
C3 Si1 C2 119.66(14) . .
C1 Si1 C2 103.87(16) . .
C3 Si1 C6 106.60(13) . .
C1 Si1 C6 110.40(15) . .
C2 Si1 C6 102.06(14) . .
C14 Si2 C12 112.95(15) . .
C14 Si2 C13 118.93(14) . .
C12 Si2 C13 104.91(18) . .
C14 Si2 C17 107.77(13) . .
C12 Si2 C17 110.18(15) . .
C13 Si2 C17 101.38(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 Si1 1.885(3) .
C2 Si1 1.897(3) .
C3 C4 1.547(4) .
C3 Si1 1.806(3) .
C3 Li1 2.258(5) 2_775
C3 Li1 2.285(5) .
C4 C5 1.522(4) .
C6 N1 1.489(4) .
C6 Si1 1.911(3) .
C7 N1 1.475(4) .
C8 N1 1.471(3) .
C8 C9 1.515(4) .
C9 N2 1.463(4) .
C10 N2 1.472(4) .
C11 N2 1.465(4) .
C12 Si2 1.886(3) .
C13 Si2 1.895(3) .
C14 C15 1.532(4) .
C14 Si2 1.813(3) .
C14 Li2 2.249(5) 2_766
C14 Li2 2.276(5) .
C15 C16 1.517(4) .
C17 N3 1.491(3) .
C17 Si2 1.905(3) .
C18 N3 1.472(4) .
C19 N3 1.473(4) .
C19 C20 1.507(5) .
C20 N4 1.474(4) .
C21 N4 1.463(4) .
C22 N4 1.468(4) .
Li1 N1 2.125(5) .
Li1 C3 2.258(5) 2_775
Li1 N2 2.349(5) .
Li1 Li1 2.548(9) 2_775
Li2 N3 2.136(5) .
Li2 C14 2.249(5) 2_766
Li2 N4 2.326(5) .
Li2 Li2 2.578(9) 2_766
