#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:14:18 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178942 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/71/4117109.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_4117109
loop_
_publ_author_name
'Klas Sorger'
'Paul von Ragué Schleyer'
'Dietmar Stalke'
_publ_section_title
;
 Dimeric [3,3-Dimethyl-2-(trimethylsilyl)cyclopropenyl]-
 lithium-Tetramethylethylenediamine: Distortion of the Cyclopropenyl
 Geometry Due to Strong Rehybridization at the Lithiated Carbon
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1086
_journal_page_last               1091
_journal_paper_doi               10.1021/ja9521280
_journal_volume                  118
_journal_year                    1996
_chemical_formula_sum            'C20 H40 Li2 N2 O'
_chemical_formula_weight         338.42
_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
_cell_angle_alpha                104.92(3)
_cell_angle_beta                 109.44(3)
_cell_angle_gamma                100.15(3)
_cell_formula_units_Z            2
_cell_length_a                   8.756(2)
_cell_length_b                   11.058(2)
_cell_length_c                   12.495(3)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     1055.9(6)
_computing_cell_refinement       DIF4
_computing_data_collection       DIF4
_computing_data_reduction        REDU4
_computing_molecular_graphics    'SHELXL-93 (Sheldrick, 1993)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       Stoe-Huber-Eigenbau
_diffrn_measurement_method       'profile fitted 2theta/omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7265
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.063
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_description       blocks
_exptl_crystal_F_000             376
_exptl_crystal_size_max          .7
_exptl_crystal_size_mid          .6
_exptl_crystal_size_min          .6
_refine_diff_density_max         .340
_refine_diff_density_min         -.363
_refine_diff_density_rms         .096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.085
_refine_ls_goodness_of_fit_obs   1.117
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_restrained_S_obs      1.117
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_obs          0.0517
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s²(Fo²)+( 0.1096P)²+0.2025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1749
_refine_ls_wR_factor_obs         0.1630
_reflns_number_observed          4043
_reflns_number_total             4896
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja9521280_3.cif
_cod_data_source_block           frank
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.1096P)^2^+0.2025P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=1/[s^2^(Fo^2^)+( 0.1096P)^2^+0.2025P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1055.9(4)
_cod_database_code               4117109
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Li1 Li 0.6437(3) 1.1330(2) 0.2424(2) 0.0240(5) Uani 1 d .
Li2 Li 0.3605(3) 0.9889(2) -0.0353(2) 0.0216(4) Uani 1 d .
O1 O 0.49658(11) 0.97160(8) 0.11407(8) 0.0182(2) Uani 1 d .
C1 C 0.2481(2) 0.78847(12) -0.13268(11) 0.0200(3) Uani 1 d .
C2 C 0.27470(15) 0.78175(12) -0.02405(11) 0.0177(3) Uani 1 d .
C3 C 0.1238(2) 0.67839(13) -0.11907(12) 0.0230(3) Uani 1 d .
C4 C -0.0559(2) 0.6839(2) -0.14193(15) 0.0359(4) Uani 1 d .
H4A H -0.1002(6) 0.6379(11) -0.0964(9) 0.048(2) Uiso 1 calc R
H4B H -0.1269(4) 0.6421(11) -0.2283(2) 0.048(2) Uiso 1 calc R
H4C H -0.0564(3) 0.7753(2) -0.1158(11) 0.048(2) Uiso 1 calc R
C5 C 0.1259(2) 0.53747(14) -0.16320(14) 0.0347(4) Uani 1 d .
H5A H 0.0516(13) 0.4968(4) -0.2491(3) 0.048(2) Uiso 1 calc R
H5B H 0.0859(15) 0.4895(3) -0.1172(8) 0.048(2) Uiso 1 calc R
H5C H 0.2415(4) 0.5351(2) -0.1519(11) 0.048(2) Uiso 1 calc R
C6 C 0.3988(2) 0.85098(12) 0.10732(11) 0.0178(3) Uani 1 d .
C7 C 0.5228(2) 0.76519(14) 0.14092(13) 0.0275(3) Uani 1 d .
C8 C 0.6679(2) 0.8307(2) 0.2646(2) 0.0438(4) Uani 1 d .
H8A H 0.6250(4) 0.8289(13) 0.3275(2) 0.060(2) Uiso 1 calc R
H8B H 0.7183(12) 0.9215(5) 0.2747(5) 0.060(2) Uiso 1 calc R
H8C H 0.7538(9) 0.7837(9) 0.2713(5) 0.060(2) Uiso 1 calc R
C9 C 0.4348(3) 0.6301(2) 0.1371(2) 0.0522(5) Uani 1 d .
H9A H 0.5127(7) 0.5761(5) 0.1417(13) 0.060(2) Uiso 1 calc R
H9B H 0.3341(11) 0.5878(6) 0.0615(6) 0.060(2) Uiso 1 calc R
H9C H 0.4014(16) 0.6402(2) 0.2056(8) 0.060(2) Uiso 1 calc R
C10 C 0.6068(2) 0.7437(2) 0.0509(2) 0.0465(5) Uani 1 d .
H10A H 0.5196(3) 0.7078(13) -0.0316(2) 0.060(2) Uiso 1 calc R
H10B H 0.6732(14) 0.6823(11) 0.0645(8) 0.060(2) Uiso 1 calc R
H10C H 0.6814(14) 0.8272(3) 0.0620(8) 0.060(2) Uiso 1 calc R
C11 C 0.2912(2) 0.88226(14) 0.18623(12) 0.0254(3) Uani 1 d .
C12 C 0.1588(2) 0.7623(2) 0.1741(2) 0.0425(4) Uani 1 d .
H12A H 0.2154(3) 0.7121(8) 0.2204(11) 0.060(2) Uiso 1 calc R
H12B H 0.0993(13) 0.7073(7) 0.0889(2) 0.060(2) Uiso 1 calc R
H12C H 0.0775(11) 0.7911(2) 0.2053(12) 0.060(2) Uiso 1 calc R
C13 C 0.3989(2) 0.9529(2) 0.32118(13) 0.0347(4) Uani 1 d .
H13A H 0.4928(10) 1.0243(9) 0.33189(13) 0.060(2) Uiso 1 calc R
H13B H 0.4438(15) 0.8911(4) 0.3573(3) 0.060(2) Uiso 1 calc R
H13C H 0.3290(5) 0.9886(12) 0.3607(3) 0.060(2) Uiso 1 calc R
C14 C 0.1947(2) 0.9748(2) 0.1420(2) 0.0365(4) Uani 1 d .
H14A H 0.1223(13) 0.9330(6) 0.0559(3) 0.060(2) Uiso 1 calc R
H14B H 0.2755(2) 1.0560(6) 0.1546(12) 0.060(2) Uiso 1 calc R
H14C H 0.1247(14) 0.9946(11) 0.1874(9) 0.060(2) Uiso 1 calc R
C15 C 0.4404(2) 1.2863(2) 0.4123(2) 0.0353(4) Uani 1 d .
H15A H 0.3328(2) 1.2431(10) 0.3420(2) 0.0417(15) Uiso 1 calc R
H15B H 0.4384(9) 1.3725(2) 0.4572(9) 0.0417(15) Uiso 1 calc R
H15C H 0.4570(8) 1.2332(10) 0.4647(9) 0.0417(15) Uiso 1 calc R
C16 C 0.5527(2) 1.3815(2) 0.2949(2) 0.0370(4) Uani 1 d .
H16A H 0.4445(7) 1.3387(6) 0.2253(6) 0.0417(15) Uiso 1 calc R
H16B H 0.6446(8) 1.3923(10) 0.2668(9) 0.0417(15) Uiso 1 calc R
H16C H 0.5513(15) 1.4674(4) 0.3409(3) 0.0417(15) Uiso 1 calc R
N1 N 0.57914(15) 1.30157(12) 0.37172(11) 0.0257(3) Uani 1 d .
C17 C 0.7407(2) 1.36341(15) 0.47669(13) 0.0302(3) Uani 1 d .
H17A H 0.7337(2) 1.33451(15) 0.54405(13) 0.036(2) Uiso 1 calc R
H17B H 0.7614(2) 1.45939(15) 0.50286(13) 0.036(2) Uiso 1 calc R
C18 C 0.8875(2) 1.33019(14) 0.44975(13) 0.0271(3) Uani 1 d .
H18A H 0.8970(2) 1.36201(14) 0.38440(13) 0.036(2) Uiso 1 calc R
H18B H 0.9935(2) 1.37620(14) 0.52251(13) 0.036(2) Uiso 1 calc R
N2 N 0.86888(14) 1.18925(12) 0.41325(10) 0.0221(3) Uani 1 d .
C19 C 0.8659(2) 1.1393(2) 0.51038(13) 0.0315(3) Uani 1 d .
H19A H 0.8717(15) 1.0490(4) 0.4890(5) 0.0417(15) Uiso 1 calc R
H19B H 0.7610(7) 1.1419(11) 0.5219(7) 0.0417(15) Uiso 1 calc R
H19C H 0.9630(8) 1.1936(7) 0.5853(3) 0.0417(15) Uiso 1 calc R
C20 C 1.0135(2) 1.1673(2) 0.38520(14) 0.0320(3) Uani 1 d .
H20A H 1.0015(8) 1.0734(2) 0.3584(10) 0.0417(15) Uiso 1 calc R
H20B H 1.1181(2) 1.2123(10) 0.4575(3) 0.0417(15) Uiso 1 calc R
H20C H 1.0175(9) 1.2015(10) 0.3209(8) 0.0417(15) Uiso 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -.0003 .0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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
O1 Li1 C1 95.84(10) . 2_675 yes
O1 Li1 N2 136.31(13) . . yes
C1 Li1 N2 101.43(10) 2_675 . yes
O1 Li1 N1 130.53(12) . . yes
C1 Li1 N1 110.37(11) 2_675 . yes
N2 Li1 N1 79.61(9) . . yes
O1 Li1 Li2 46.91(8) . 2_675 ?
C1 Li1 Li2 51.61(8) 2_675 2_675 ?
N2 Li1 Li2 122.65(12) . 2_675 ?
N1 Li1 Li2 151.32(12) . 2_675 ?
O1 Li1 Li2 31.91(6) . . ?
C1 Li1 Li2 74.97(8) 2_675 . ?
N2 Li1 Li2 164.04(11) . . ?
N1 Li1 Li2 116.30(10) . . ?
Li2 Li1 Li2 43.06(9) 2_675 . ?
O1 Li2 O1 107.95(11) 2_675 . yes
O1 Li2 C1 99.82(11) 2_675 . yes
O1 Li2 C1 96.92(11) . . yes
O1 Li2 Li2 54.78(9) 2_675 2_675 ?
O1 Li2 Li2 53.17(10) . 2_675 ?
C1 Li2 Li2 104.3(2) . 2_675 ?
O1 Li2 C2 123.15(12) 2_675 . yes
O1 Li2 C2 66.75(9) . . yes
C1 Li2 C2 34.16(6) . . yes
Li2 Li2 C2 96.96(14) 2_675 . ?
O1 Li2 Li1 48.49(8) 2_675 2_675 ?
O1 Li2 Li1 123.77(12) . 2_675 ?
C1 Li2 Li1 54.21(8) . 2_675 ?
Li2 Li2 Li1 85.39(14) 2_675 2_675 ?
C2 Li2 Li1 85.85(10) . 2_675 ?
O1 Li2 C6 126.17(11) 2_675 . ?
O1 Li2 C6 32.25(5) . . ?
C1 Li2 C6 68.48(8) . . ?
Li2 Li2 C6 76.72(12) 2_675 . ?
C2 Li2 C6 35.46(5) . . ?
Li1 Li2 C6 112.64(10) 2_675 . ?
O1 Li2 Li1 97.22(10) 2_675 . ?
O1 Li2 Li1 32.08(6) . . ?
C1 Li2 Li1 128.94(11) . . ?
Li2 Li2 Li1 51.54(11) 2_675 . ?
C2 Li2 Li1 98.04(10) . . ?
Li1 Li2 Li1 136.94(9) 2_675 . ?
C6 Li2 Li1 62.64(7) . . ?
C6 O1 Li2 131.74(10) . 2_675 yes
C6 O1 Li2 101.19(10) . . yes
Li2 O1 Li2 72.05(11) 2_675 . yes
C6 O1 Li1 135.59(10) . . yes
Li2 O1 Li1 84.60(11) 2_675 . yes
Li2 O1 Li1 116.01(11) . . yes
C2 C1 C3 60.83(9) . . yes
C2 C1 Li2 82.80(10) . . ?
C3 C1 Li2 133.28(11) . . ?
C2 C1 Li1 145.91(12) . 2_675 ?
C3 C1 Li1 150.67(11) . 2_675 ?
Li2 C1 Li1 74.18(10) . 2_675 ?
C1 C2 C3 67.80(10) . . yes
C1 C2 C6 140.22(11) . . yes
C3 C2 C6 151.98(11) . . yes
C1 C2 Li2 63.04(10) . . ?
C3 C2 Li2 122.68(11) . . ?
C6 C2 Li2 81.96(9) . . ?
C2 C3 C4 123.30(13) . . yes
C2 C3 C5 121.68(13) . . yes
C4 C3 C5 110.05(13) . . yes
C2 C3 C1 51.37(8) . . yes
C4 C3 C1 119.10(12) . . yes
C5 C3 C1 119.80(12) . . yes
O1 C6 C2 107.19(10) . . yes
O1 C6 C7 107.72(10) . . ?
C2 C6 C7 108.04(10) . . ?
O1 C6 C11 107.89(10) . . ?
C2 C6 C11 107.67(10) . . ?
C7 C6 C11 117.88(11) . . ?
O1 C6 Li2 46.56(7) . . ?
C2 C6 Li2 62.58(8) . . ?
C7 C6 Li2 132.87(10) . . ?
C11 C6 Li2 108.50(10) . . ?
C8 C7 C10 105.34(14) . . ?
C8 C7 C9 106.94(14) . . ?
C10 C7 C9 107.6(2) . . ?
C8 C7 C6 113.88(12) . . ?
C10 C7 C6 108.61(12) . . ?
C9 C7 C6 113.97(13) . . ?
C13 C11 C14 106.50(13) . . ?
C13 C11 C12 107.31(12) . . ?
C14 C11 C12 106.96(14) . . ?
C13 C11 C6 113.87(12) . . ?
C14 C11 C6 107.15(11) . . ?
C12 C11 C6 114.54(12) . . ?
C16 N1 C15 108.56(13) . . ?
C16 N1 C17 110.60(13) . . ?
C15 N1 C17 109.63(12) . . ?
C16 N1 Li1 97.01(10) . . ?
C15 N1 Li1 127.43(11) . . ?
C17 N1 Li1 102.56(10) . . ?
N1 C17 C18 112.31(11) . . ?
N2 C18 C17 112.67(12) . . ?
C19 N2 C20 108.81(12) . . ?
C19 N2 C18 111.07(12) . . ?
C20 N2 C18 108.31(12) . . ?
C19 N2 Li1 122.06(11) . . ?
C20 N2 Li1 109.12(11) . . ?
C18 N2 Li1 96.36(11) . . ?
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
Li1 O1 1.938(3) . yes
Li1 C1 2.173(3) 2_675 yes
Li1 N2 2.217(3) . yes
Li1 N1 2.415(3) . yes
Li1 Li2 2.577(3) 2_675 ?
Li1 Li2 3.281(4) . ?
Li2 O1 1.891(2) 2_675 yes
Li2 O1 1.930(3) . yes
Li2 C1 2.100(3) . yes
Li2 Li2 2.247(4) 2_675 ?
Li2 C2 2.337(3) . yes
Li2 Li1 2.577(3) 2_675 ?
Li2 C6 2.607(3) . ?
O1 C6 1.4181(15) . yes
O1 Li2 1.891(2) 2_675 ?
C1 C2 1.323(2) . yes
C1 C3 1.568(2) . yes
C1 Li1 2.173(3) 2_675 ?
C2 C3 1.479(2) . yes
C2 C6 1.528(2) . yes
C3 C4 1.518(2) . yes
C3 C5 1.519(2) . yes
C6 C7 1.588(2) . yes
C6 C11 1.593(2) . yes
C7 C8 1.523(2) . ?
C7 C10 1.529(2) . ?
C7 C9 1.537(2) . ?
C11 C13 1.532(2) . ?
C11 C14 1.534(2) . ?
C11 C12 1.537(2) . ?
C15 N1 1.464(2) . ?
C16 N1 1.455(2) . ?
N1 C17 1.467(2) . ?
C17 C18 1.514(2) . ?
C18 N2 1.469(2) . ?
N2 C19 1.463(2) . ?
N2 C20 1.464(2) . ?
