#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:15:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179683 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/05/7000548.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_7000548
loop_
_publ_author_name
'Melero, Cristóbal'
'Guijarro, Albert'
'Yus, Miguel'
_publ_section_title
;
 Structural characterization and bonding properties of lithium
 naphthalene radical anion, [Li+(TMEDA)2][C10H8˙−], and
 lithium naphthalene dianion [(Li+TMEDA)2C10H8−2]
;
_journal_issue                   8
_journal_name_full               'Dalton Transactions'
_journal_page_first              1286
_journal_paper_doi               10.1039/b821119c
_journal_year                    2009
_chemical_formula_moiety         'C22 H40 Li2 N4, C6 H6'
_chemical_formula_sum            'C28 H46 Li2 N4'
_chemical_formula_weight         452.57
_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                101.930(2)
_cell_angle_beta                 98.277(2)
_cell_angle_gamma                109.538(2)
_cell_formula_units_Z            1
_cell_length_a                   8.7009(9)
_cell_length_b                   9.0075(9)
_cell_length_c                   10.1014(11)
_cell_measurement_reflns_used    3511
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.45
_cell_volume                     710.22(13)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7324
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0748P)²+0.1627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                2837
_reflns_number_total             3261
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b821119c.txt
_cod_data_source_block           Compound_2
_cod_database_code               7000548
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
Li1 Li 0.8323(2) 0.0678(2) 0.1687(2) 0.0305(4) Uani 1 1 d . . .
N1 N 0.76449(12) 0.14517(12) 0.35712(10) 0.0300(2) Uani 1 1 d . . .
C1 C 0.58511(17) 0.05332(17) 0.33490(16) 0.0429(3) Uani 1 1 d . . .
H1A H 0.5652 -0.0600 0.3267 0.064 Uiso 1 1 calc R . .
H1B H 0.5268 0.0634 0.2511 0.064 Uiso 1 1 calc R . .
H1C H 0.5454 0.0961 0.4123 0.064 Uiso 1 1 calc R . .
C2 C 0.8533(2) 0.1240(2) 0.48116(15) 0.0525(4) Uani 1 1 d . . .
H2A H 0.8154 0.1651 0.5604 0.079 Uiso 1 1 calc R . .
H2B H 0.9715 0.1830 0.4953 0.079 Uiso 1 1 calc R . .
H2C H 0.8315 0.0097 0.4696 0.079 Uiso 1 1 calc R . .
C3 C 0.79959(16) 0.31994(15) 0.37283(13) 0.0356(3) Uani 1 1 d . . .
H3A H 0.9189 0.3816 0.4092 0.043 Uiso 1 1 calc R . .
H3B H 0.7415 0.3575 0.4394 0.043 Uiso 1 1 calc R . .
C4 C 0.74517(15) 0.35271(14) 0.23664(13) 0.0329(3) Uani 1 1 d . . .
H4A H 0.6240 0.3029 0.2061 0.040 Uiso 1 1 calc R . .
H4B H 0.7783 0.4698 0.2501 0.040 Uiso 1 1 calc R . .
N2 N 0.81997(12) 0.28707(12) 0.12936(10) 0.0284(2) Uani 1 1 d . . .
C5 C 0.99465(15) 0.39449(16) 0.14775(15) 0.0393(3) Uani 1 1 d . . .
H5A H 0.9997 0.5011 0.1424 0.059 Uiso 1 1 calc R . .
H5B H 1.0408 0.3496 0.0760 0.059 Uiso 1 1 calc R . .
H5C H 1.0581 0.4032 0.2370 0.059 Uiso 1 1 calc R . .
C6 C 0.72505(18) 0.26933(18) -0.00847(14) 0.0411(3) Uani 1 1 d . . .
H6A H 0.6112 0.1961 -0.0219 0.062 Uiso 1 1 calc R . .
H6B H 0.7747 0.2258 -0.0781 0.062 Uiso 1 1 calc R . .
H6C H 0.7269 0.3744 -0.0160 0.062 Uiso 1 1 calc R . .
C7 C 1.07203(12) 0.02341(12) 0.05734(10) 0.0232(2) Uani 1 1 d . . .
C8 C 1.04363(14) -0.03393(14) 0.17600(11) 0.0279(2) Uani 1 1 d . . .
H8 H 1.1263 0.0128 0.2582 0.033 Uiso 1 1 calc R . .
C9 C 0.88991(15) -0.16256(14) 0.17136(12) 0.0310(3) Uani 1 1 d . . .
H9 H 0.8825 -0.2164 0.2409 0.037 Uiso 1 1 calc R . .
C10 C 0.75479(14) -0.20536(14) 0.06437(13) 0.0313(3) Uani 1 1 d . . .
H10 H 0.6539 -0.2874 0.0609 0.038 Uiso 1 1 calc R . .
C11 C 0.76980(13) -0.12238(13) -0.04300(11) 0.0281(2) Uani 1 1 d . . .
H11 H 0.6734 -0.1340 -0.1045 0.034 Uiso 1 1 calc R . .
C12 C 0.4139(2) 0.37983(19) 0.5541(2) 0.0572(4) Uani 1 1 d . . .
H12 H 0.3552 0.2976 0.5910 0.069 Uiso 1 1 calc R . .
C13 C 0.36000(18) 0.37187(19) 0.41764(19) 0.0550(4) Uani 1 1 d . . .
H13 H 0.2648 0.2846 0.3625 0.066 Uiso 1 1 calc R . .
C14 C 0.4450(2) 0.4908(2) 0.36265(18) 0.0552(4) Uani 1 1 d . . .
H14 H 0.4089 0.4855 0.2699 0.066 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'
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
_geom_angle_publ_flag
N1 Li1 N2 85.24(8) . . ?
N1 Li1 C10 120.13(10) . . ?
N2 Li1 C10 142.05(10) . . ?
N1 Li1 C9 108.43(9) . . ?
N2 Li1 C9 165.12(10) . . ?
C10 Li1 C9 34.60(5) . . ?
N1 Li1 C11 149.09(10) . . ?
N2 Li1 C11 107.88(9) . . ?
C10 Li1 C11 36.41(5) . . ?
C9 Li1 C11 63.30(6) . . ?
N1 Li1 C8 118.51(9) . . ?
N2 Li1 C8 131.89(10) . . ?
C10 Li1 C8 63.41(6) . . ?
C9 Li1 C8 36.27(5) . . ?
C11 Li1 C8 73.77(7) . . ?
N1 Li1 C7 177.73(10) . 2_755 ?
N2 Li1 C7 95.22(8) . 2_755 ?
C10 Li1 C7 60.60(6) . 2_755 ?
C9 Li1 C7 70.88(6) . 2_755 ?
C11 Li1 C7 32.69(4) . 2_755 ?
C8 Li1 C7 59.62(6) . 2_755 ?
N1 Li1 C7 145.39(10) . . ?
N2 Li1 C7 104.90(8) . . ?
C10 Li1 C7 71.09(6) . . ?
C9 Li1 C7 60.52(6) . . ?
C11 Li1 C7 59.54(6) . . ?
C8 Li1 C7 32.84(4) . . ?
C7 Li1 C7 32.36(5) 2_755 . ?
C2 N1 C1 109.31(11) . . ?
C2 N1 C3 109.87(11) . . ?
C1 N1 C3 110.84(10) . . ?
C2 N1 Li1 116.24(10) . . ?
C1 N1 Li1 106.58(9) . . ?
C3 N1 Li1 103.85(9) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 111.99(10) . . ?
N1 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N2 C4 C3 111.32(9) . . ?
N2 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 N2 C5 109.36(10) . . ?
C6 N2 C4 110.04(9) . . ?
C5 N2 C4 110.92(10) . . ?
C6 N2 Li1 115.81(9) . . ?
C5 N2 Li1 104.86(9) . . ?
C4 N2 Li1 105.72(8) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C11 C7 C8 124.61(10) 2_755 . ?
C11 C7 C7 117.84(12) 2_755 2_755 ?
C8 C7 C7 117.55(12) . 2_755 ?
C11 C7 Li1 61.87(7) 2_755 2_755 ?
C8 C7 Li1 136.89(8) . 2_755 ?
C7 C7 Li1 73.90(9) 2_755 2_755 ?
C11 C7 Li1 136.99(8) 2_755 . ?
C8 C7 Li1 61.85(7) . . ?
C7 C7 Li1 73.74(9) 2_755 . ?
Li1 C7 Li1 147.64(5) 2_755 . ?
C7 C8 C9 121.24(10) . . ?
C7 C8 Li1 85.31(8) . . ?
C9 C8 Li1 71.29(8) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
Li1 C8 H8 114.2 . . ?
C10 C9 C8 119.52(10) . . ?
C10 C9 Li1 72.36(8) . . ?
C8 C9 Li1 72.44(8) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
Li1 C9 H9 126.9 . . ?
C9 C10 C11 119.32(10) . . ?
C9 C10 Li1 73.04(8) . . ?
C11 C10 Li1 72.61(8) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
Li1 C10 H10 125.8 . . ?
C7 C11 C10 121.46(10) 2_755 . ?
C7 C11 Li1 85.44(8) 2_755 . ?
C10 C11 Li1 70.97(8) . . ?
C7 C11 H11 119.3 2_755 . ?
C10 C11 H11 119.3 . . ?
Li1 C11 H11 114.5 . . ?
C13 C12 C14 120.52(16) . 2_666 ?
C13 C12 H12 119.7 . . ?
C14 C12 H12 119.7 2_666 . ?
C14 C13 C12 120.20(15) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C12 119.28(16) . 2_666 ?
C13 C14 H14 120.4 . . ?
C12 C14 H14 120.4 2_666 . ?
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 N1 2.123(2) . ?
Li1 N2 2.128(2) . ?
Li1 C10 2.287(2) . ?
Li1 C9 2.296(2) . ?
Li1 C11 2.309(2) . ?
Li1 C8 2.311(2) . ?
Li1 C7 2.610(2) 2_755 ?
Li1 C7 2.612(2) . ?
N1 C2 1.4567(16) . ?
N1 C1 1.4593(16) . ?
N1 C3 1.4690(16) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.5092(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.4640(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N2 C6 1.4610(16) . ?
N2 C5 1.4634(15) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C11 1.4142(15) 2_755 ?
C7 C8 1.4214(15) . ?
C7 C7 1.4552(19) 2_755 ?
C8 C9 1.4341(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.3630(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.4362(16) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.369(3) . ?
C12 C14 1.383(2) 2_666 ?
C12 H12 0.9300 . ?
C13 C14 1.356(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
