#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:15:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179683 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/05/7000547.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_7000547
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 Li N4'
_chemical_formula_sum            'C22 H40 Li N4'
_chemical_formula_weight         367.52
_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                 107.232(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6106(19)
_cell_length_b                   9.2603(11)
_cell_length_c                   16.937(2)
_cell_measurement_reflns_used    2641
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      2.5
_cell_volume                     2338.5(5)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9464
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.044
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0699
_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)+(0.1461P)²+2.0075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2348
_reflns_number_gt                1673
_reflns_number_total             2057
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b821119c.txt
_cod_data_source_block           Compound_1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7000547
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Li1 Li 0.5000 0.0460(5) 0.2500 0.0276(10) Uani 1 2 d S . .
N1 N 0.43198(13) 0.2097(2) 0.29577(12) 0.0394(6) Uani 1 1 d . . .
C1 C 0.3429(2) 0.2238(4) 0.2387(2) 0.0650(9) Uani 1 1 d . . .
H1A H 0.3064 0.1446 0.2463 0.098 Uiso 1 1 calc R . .
H1B H 0.3463 0.2230 0.1831 0.098 Uiso 1 1 calc R . .
H1C H 0.3168 0.3131 0.2489 0.098 Uiso 1 1 calc R . .
C2 C 0.4254(2) 0.2007(3) 0.38015(16) 0.0542(8) Uani 1 1 d . . .
H2A H 0.3929 0.2828 0.3909 0.081 Uiso 1 1 calc R . .
H2B H 0.4845 0.1997 0.4187 0.081 Uiso 1 1 calc R . .
H2C H 0.3944 0.1138 0.3861 0.081 Uiso 1 1 calc R . .
C3 C 0.4859(2) 0.3392(3) 0.2885(2) 0.0600(8) Uani 1 1 d . . .
H3A H 0.5389 0.3432 0.3361 0.072 Uiso 1 1 calc R . .
H3B H 0.4507 0.4253 0.2892 0.072 Uiso 1 1 calc R . .
N2 N 0.57098(14) -0.1160(2) 0.33109(11) 0.0400(6) Uani 1 1 d . . .
C4 C 0.6619(2) -0.1348(4) 0.3270(2) 0.0693(10) Uani 1 1 d . . .
H4A H 0.6968 -0.0507 0.3491 0.104 Uiso 1 1 calc R . .
H4B H 0.6608 -0.1479 0.2705 0.104 Uiso 1 1 calc R . .
H4C H 0.6883 -0.2181 0.3587 0.104 Uiso 1 1 calc R . .
C5 C 0.5754(2) -0.1018(3) 0.41856(15) 0.0479(7) Uani 1 1 d . . .
H5A H 0.6065 -0.1834 0.4488 0.072 Uiso 1 1 calc R . .
H5B H 0.5158 -0.0979 0.4235 0.072 Uiso 1 1 calc R . .
H5C H 0.6070 -0.0148 0.4406 0.072 Uiso 1 1 calc R . .
C6 C 0.5144(2) -0.2448(3) 0.29639(16) 0.0532(8) Uani 1 1 d . . .
H6A H 0.4616 -0.2448 0.3155 0.064 Uiso 1 1 calc R . .
H6B H 0.5481 -0.3321 0.3165 0.064 Uiso 1 1 calc R . .
C7 C 0.73856(14) 0.1978(2) 0.52700(13) 0.0331(6) Uani 1 1 d . . .
C8 C 0.78729(16) 0.0670(3) 0.54245(15) 0.0413(6) Uani 1 1 d . . .
H8 H 0.7740 -0.0004 0.5778 0.050 Uiso 1 1 calc R . .
C9 C 0.85466(17) 0.0360(3) 0.50632(16) 0.0450(7) Uani 1 1 d . . .
H9 H 0.8848 -0.0519 0.5170 0.054 Uiso 1 1 calc R . .
C10 C 0.87681(16) 0.1356(3) 0.45468(15) 0.0433(7) Uani 1 1 d . . .
H10 H 0.9218 0.1150 0.4307 0.052 Uiso 1 1 calc R . .
C11 C 0.83122(16) 0.2672(3) 0.43883(15) 0.0410(6) Uani 1 1 d . . .
H11 H 0.8473 0.3340 0.4047 0.049 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
N2 Li1 N2 89.5(2) 2_655 . ?
N2 Li1 N1 121.42(8) 2_655 . ?
N2 Li1 N1 119.47(7) . . ?
N1 Li1 N1 89.0(2) 2_655 . ?
C1 N1 C2 109.0(2) . . ?
C1 N1 C3 109.1(2) . . ?
C2 N1 C3 109.3(2) . . ?
C1 N1 Li1 107.84(17) . . ?
C2 N1 Li1 120.18(17) . . ?
C3 N1 Li1 100.86(17) . . ?
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 C3 113.1(2) . 2_655 ?
N1 C3 H3A 109.0 . . ?
C3 C3 H3A 109.0 2_655 . ?
N1 C3 H3B 109.0 . . ?
C3 C3 H3B 109.0 2_655 . ?
H3A C3 H3B 107.8 . . ?
C4 N2 C5 107.7(2) . . ?
C4 N2 C6 111.0(2) . . ?
C5 N2 C6 108.28(19) . . ?
C4 N2 Li1 112.69(17) . . ?
C5 N2 Li1 116.82(17) . . ?
C6 N2 Li1 100.10(17) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
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 C6 111.69(19) . 2_655 ?
N2 C6 H6A 109.3 . . ?
C6 C6 H6A 109.3 2_655 . ?
N2 C6 H6B 109.3 . . ?
C6 C6 H6B 109.3 2_655 . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C11 123.9(2) . 7_656 ?
C8 C7 C7 118.0(3) . 7_656 ?
C11 C7 C7 118.0(3) 7_656 7_656 ?
C9 C8 C7 122.0(2) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C7 122.1(2) . 7_656 ?
C10 C11 H11 118.9 . . ?
C7 C11 H11 118.9 7_656 . ?
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 N2 2.113(4) . ?
Li1 N1 2.125(4) . ?
N1 C1 1.445(4) . ?
N1 C2 1.465(3) . ?
N1 C3 1.491(4) . ?
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 C3 1.495(6) 2_655 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N2 C4 1.452(4) . ?
N2 C5 1.468(3) . ?
N2 C6 1.497(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C6 1.501(5) 2_655 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.413(3) . ?
C7 C11 1.414(3) 7_656 ?
C7 C7 1.446(4) 7_656 ?
C8 C9 1.394(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.397(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
