#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:44:17 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178665 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/76/4077636.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_4077636
loop_
_publ_author_name
'Rabe, Gerd W.'
'Sommer, Roger D.'
'Rheingold, Arnold L.'
_publ_section_title
;
 Synthesis and X-ray Crystal Structure Determination of Tetrahydrofuran
 Adducts of Two Terphenyllithium Compounds†
;
_journal_issue                   25
_journal_name_full               Organometallics
_journal_page_first              5537
_journal_paper_doi               10.1021/om0006864
_journal_volume                  19
_journal_year                    2000
_chemical_formula_sum            'C40 H34 Li2 O'
_chemical_formula_weight         544.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.176(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3391(10)
_cell_length_b                   15.5925(13)
_cell_length_c                   16.5319(14)
_cell_measurement_reflns_used    3198
_cell_measurement_temperature    173(2)
_cell_volume                     3120.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.824
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6722
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_type   'Empirical from SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0575P)²+4.5809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2031
_reflns_number_total             2528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om0006864.cif
_cod_data_source_block           rab25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4077636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.6456(2) -0.17215(13) 0.73729(12) 0.0264(5) Uani 1 1 d .
C2 C 0.6747(2) -0.20721(13) 0.66476(12) 0.0261(5) Uani 1 1 d .
C3 C 0.7707(2) -0.18574(14) 0.63737(13) 0.0309(6) Uani 1 1 d .
H3A H 0.7852 -0.2099 0.5878 0.037 Uiso 1 1 calc R
C4 C 0.8451(2) -0.12913(15) 0.68231(14) 0.0347(6) Uani 1 1 d .
H4A H 0.9110 -0.1143 0.6640 0.042 Uiso 1 1 calc R
C5 C 0.8228(2) -0.09432(14) 0.75422(14) 0.0327(6) Uani 1 1 d .
H5A H 0.8740 -0.0558 0.7856 0.039 Uiso 1 1 calc R
C6 C 0.7258(2) -0.11527(13) 0.78118(12) 0.0272(5) Uani 1 1 d .
C7 C 0.5966(2) -0.27070(13) 0.61627(12) 0.0272(5) Uani 1 1 d .
C8 C 0.5590(2) -0.34051(14) 0.65540(14) 0.0304(6) Uani 1 1 d .
H8A H 0.5894(19) -0.3499(14) 0.7137(14) 0.028(6) Uiso 1 1 d .
C9 C 0.4826(2) -0.39806(15) 0.61233(15) 0.0389(7) Uani 1 1 d .
H9A H 0.4566 -0.4446 0.6404 0.047 Uiso 1 1 calc R
C10 C 0.4447(2) -0.38712(16) 0.52856(15) 0.0447(7) Uani 1 1 d .
H10A H 0.3928 -0.4263 0.4988 0.054 Uiso 1 1 calc R
C11 C 0.4826(2) -0.31903(16) 0.48849(14) 0.0419(7) Uani 1 1 d .
H11A H 0.4567 -0.3115 0.4310 0.050 Uiso 1 1 calc R
C12 C 0.5582(2) -0.26155(15) 0.53156(13) 0.0341(6) Uani 1 1 d .
H12A H 0.5842 -0.2153 0.5030 0.041 Uiso 1 1 calc R
C13 C 0.7055(2) -0.07514(14) 0.85929(13) 0.0279(5) Uani 1 1 d .
C14 C 0.6552(2) -0.12091(15) 0.91415(14) 0.0368(6) Uani 1 1 d .
H14A H 0.6332 -0.1786 0.9020 0.044 Uiso 1 1 calc R
C15 C 0.6367(3) -0.08347(18) 0.98647(15) 0.0476(8) Uani 1 1 d .
H15A H 0.6013 -0.1155 1.0228 0.057 Uiso 1 1 calc R
C16 C 0.6693(2) 0.00014(17) 1.00620(15) 0.0453(7) Uani 1 1 d .
H16A H 0.6572 0.0254 1.0560 0.054 Uiso 1 1 calc R
C17 C 0.7196(2) 0.04613(15) 0.95264(14) 0.0370(6) Uani 1 1 d .
H17A H 0.7422 0.1036 0.9655 0.044 Uiso 1 1 calc R
C18 C 0.7375(2) 0.00931(14) 0.88008(13) 0.0324(6) Uani 1 1 d .
H18A H 0.7721 0.0421 0.8438 0.039 Uiso 1 1 calc R
C19 C 0.5488(3) 0.07914(17) 0.69554(15) 0.0474(8) Uani 1 1 d .
H19A H 0.5216 0.0622 0.6374 0.057 Uiso 1 1 calc R
H19B H 0.6303 0.0737 0.7081 0.057 Uiso 1 1 calc R
C20 C 0.5151(4) 0.16870(19) 0.7097(2) 0.0932(15) Uani 1 1 d .
H20A H 0.5771 0.2088 0.7088 0.112 Uiso 1 1 calc R
H20B H 0.4516 0.1862 0.6666 0.112 Uiso 1 1 calc R
Li1 Li 0.5000 -0.0928(4) 0.7500 0.0557(19) Uani 1 2 d S
Li2 Li 0.5000 -0.2392(4) 0.7500 0.0451(16) Uani 1 2 d S
O1 O 0.5000 0.02636(13) 0.7500 0.0349(6) Uani 1 2 d S
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'
Li Li -0.0003 0.0001 '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'
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
C6 C1 C2 113.9(2) . .
C6 C1 Li2 140.93(18) . .
C2 C1 Li2 104.50(17) . .
C6 C1 Li1 95.72(17) . .
C2 C1 Li1 129.24(15) . .
Li2 C1 Li1 63.31(19) . .
C3 C2 C1 123.5(2) . .
C3 C2 C7 119.0(2) . .
C1 C2 C7 117.5(2) . .
C4 C3 C2 119.9(2) . .
C3 C4 C5 119.4(2) . .
C4 C5 C6 120.6(2) . .
C5 C6 C1 122.7(2) . .
C5 C6 C13 118.3(2) . .
C1 C6 C13 119.0(2) . .
C5 C6 Li1 144.06(17) . .
C1 C6 Li1 53.46(16) . .
C13 C6 Li1 77.11(14) . .
C8 C7 C12 117.9(2) . .
C8 C7 C2 120.37(18) . .
C12 C7 C2 121.8(2) . .
C8 C7 Li2 61.98(16) . .
C12 C7 Li2 132.22(17) . .
C2 C7 Li2 77.68(14) . .
C7 C8 C9 121.3(2) . .
C7 C8 Li2 87.68(16) . .
C9 C8 Li2 119.35(19) . .
C10 C9 C8 119.7(2) . .
C11 C10 C9 119.7(2) . .
C10 C11 C12 120.5(2) . .
C11 C12 C7 120.9(2) . .
C14 C13 C18 117.6(2) . .
C14 C13 C6 121.15(19) . .
C18 C13 C6 121.3(2) . .
C15 C14 C13 120.9(2) . .
C16 C15 C14 120.7(2) . .
C17 C16 C15 119.0(2) . .
C16 C17 C18 120.5(2) . .
C17 C18 C13 121.2(2) . .
O1 C19 C20 106.0(3) . .
C20 C20 C19 105.90(18) 2_656 .
O1 Li1 C1 123.81(13) . 2_656
O1 Li1 C1 123.81(13) . .
C1 Li1 C1 112.4(3) 2_656 .
O1 Li1 Li2 180.000(1) . .
C1 Li1 Li2 56.19(13) 2_656 .
C1 Li1 Li2 56.19(13) . .
O1 Li1 C6 97.32(12) . .
C1 Li1 C6 135.8(2) 2_656 .
C1 Li1 C6 30.83(7) . .
Li2 Li1 C6 82.68(12) . .
O1 Li1 C6 97.32(12) . 2_656
C1 Li1 C6 30.83(7) 2_656 2_656
C1 Li1 C6 135.8(2) . 2_656
Li2 Li1 C6 82.68(12) . 2_656
C6 Li1 C6 165.4(2) . 2_656
C1 Li2 C1 121.0(3) . 2_656
C1 Li2 Li1 60.50(14) . .
C1 Li2 Li1 60.50(14) 2_656 .
C1 Li2 C8 138.40(10) . 2_656
C1 Li2 C8 83.80(9) 2_656 2_656
Li1 Li2 C8 130.51(11) . 2_656
C1 Li2 C8 83.80(9) . .
C1 Li2 C8 138.40(10) 2_656 .
Li1 Li2 C8 130.51(11) . .
C8 Li2 C8 99.0(2) 2_656 .
C1 Li2 C7 60.12(7) . .
C1 Li2 C7 132.36(11) 2_656 .
Li1 Li2 C7 100.27(12) . .
C8 Li2 C7 129.1(2) 2_656 .
C8 Li2 C7 30.34(7) . .
C1 Li2 C7 132.36(11) . 2_656
C1 Li2 C7 60.12(7) 2_656 2_656
Li1 Li2 C7 100.27(12) . 2_656
C8 Li2 C7 30.34(7) 2_656 2_656
C8 Li2 C7 129.1(2) . 2_656
C7 Li2 C7 159.5(2) . 2_656
C19 O1 C19 110.0(3) . 2_656
C19 O1 Li1 124.98(14) . .
C19 O1 Li1 124.98(14) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.419(3) .
C1 C2 1.426(3) .
C1 Li2 2.124(4) .
C1 Li1 2.225(4) .
C2 C3 1.388(3) .
C2 C7 1.501(3) .
C3 C4 1.382(3) .
C4 C5 1.382(3) .
C5 C6 1.395(3) .
C6 C13 1.499(3) .
C6 Li1 2.755(3) .
C7 C8 1.391(3) .
C7 C12 1.396(3) .
C7 Li2 2.752(2) .
C8 C9 1.393(3) .
C8 Li2 2.431(4) .
C9 C10 1.384(3) .
C10 C11 1.380(4) .
C11 C12 1.387(3) .
C13 C14 1.391(3) .
C13 C18 1.398(3) .
C14 C15 1.389(3) .
C15 C16 1.385(4) .
C16 C17 1.377(4) .
C17 C18 1.386(3) .
C19 O1 1.435(3) .
C19 C20 1.488(4) .
C20 C20 1.451(7) 2_656
Li1 O1 1.857(6) .
Li1 C1 2.225(4) 2_656
Li1 Li2 2.284(8) .
Li1 C6 2.755(3) 2_656
Li2 C1 2.124(4) 2_656
Li2 C8 2.431(4) 2_656
Li2 C7 2.752(2) 2_656
O1 C19 1.435(3) 2_656
