#------------------------------------------------------------------------------
#$Date: 2017-03-29 18:34:18 +0300 (Wed, 29 Mar 2017) $
#$Revision: 194593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/04/7010446.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_7010446
loop_
_publ_author_name
'Jürgen Betz'
'Frank Hampel'
'Walter Bauer'
_publ_section_title
;
 The solution and solid state structure of
 {[1-(dimethylamino)-8-naphthyl]lithium·THF}2
;
_journal_issue                   12
_journal_name_full               'J. Chem. Soc., Dalton Trans.'
_journal_page_first              1876
_journal_page_last               1879
_journal_paper_doi               10.1039/b009077h
_journal_year                    2001
_chemical_formula_sum            'C16 H20 Li N O'
_chemical_formula_weight         249.27
_chemical_name_systematic
;
 ([1-(Dimethylamino)-8-naphthyl]lithium× THF)2
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 109.222(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5897(6)
_cell_length_b                   11.7592(8)
_cell_length_c                   11.3237(7)
_cell_measurement_temperature    173(2)
_cell_volume                     1457.22(16)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       Collect
_computing_data_reduction        DENZO-SMN
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4266
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_type   SCALEPACK
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w==1/[σ²(Fo²)+(0.0943P)²+0.7975P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1709
_reflns_number_gt                1897
_reflns_number_total             2559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b009077h.txt
_cod_data_source_block
([1-(Dimethylamino)-8-naphthyl]lithium&#x00B7;THF)2
_cod_depositor_comments
;
 Replacing the "&#x00B7;" substring with the "\\times " substring in the
 _chemical_name_systematic data items value.

 Antanas Vaitkus,
 2017-03-29

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1457.22(15)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7010446
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.4314(3) -0.0289(3) 0.0499(3) 0.0385(8) Uani 1 1 d . . .
N1 N 0.60922(16) 0.20046(15) -0.00189(15) 0.0364(4) Uani 1 1 d . . .
C1 C 0.71684(18) 0.18839(18) 0.10736(19) 0.0360(5) Uani 1 1 d . . .
C2 C 0.8126(2) 0.2638(2) 0.1326(2) 0.0449(6) Uani 1 1 d . . .
H2 H 0.8096 0.3242 0.0760 0.054 Uiso 1 1 calc R . .
C3 C 0.9150(2) 0.2524(2) 0.2413(2) 0.0528(6) Uani 1 1 d . . .
H3 H 0.9811 0.3045 0.2570 0.063 Uiso 1 1 calc R . .
C4 C 0.9197(2) 0.1678(2) 0.3234(2) 0.0504(6) Uani 1 1 d . . .
H4 H 0.9880 0.1627 0.3979 0.061 Uiso 1 1 calc R . .
C5 C 0.8274(2) -0.0008(2) 0.3864(2) 0.0489(6) Uani 1 1 d . . .
H5 H 0.8944 -0.0057 0.4621 0.059 Uiso 1 1 calc R . .
C6 C 0.7354(2) -0.0777(2) 0.3622(2) 0.0489(6) Uani 1 1 d . . .
H6 H 0.7367 -0.1351 0.4218 0.059 Uiso 1 1 calc R . .
C7 C 0.6381(2) -0.0722(2) 0.2485(2) 0.0422(5) Uani 1 1 d . . .
H7 H 0.5770 -0.1294 0.2333 0.051 Uiso 1 1 calc R . .
C8 C 0.62387(18) 0.01001(18) 0.15664(18) 0.0350(5) Uani 1 1 d . . .
C9 C 0.72043(17) 0.09351(18) 0.18831(18) 0.0336(5) Uani 1 1 d . . .
C10 C 0.82439(18) 0.08655(19) 0.3002(2) 0.0397(5) Uani 1 1 d . . .
C21 C 0.6283(2) 0.2709(2) -0.1012(2) 0.0519(6) Uani 1 1 d . . .
H21A H 0.6968 0.2403 -0.1240 0.078 Uiso 1 1 calc R . .
H21B H 0.6468 0.3491 -0.0712 0.078 Uiso 1 1 calc R . .
H21C H 0.5542 0.2701 -0.1747 0.078 Uiso 1 1 calc R . .
C22 C 0.5059(2) 0.2470(2) 0.0320(2) 0.0427(6) Uani 1 1 d . . .
H22A H 0.4929 0.2003 0.0982 0.064 Uiso 1 1 calc R . .
H22B H 0.4318 0.2462 -0.0416 0.064 Uiso 1 1 calc R . .
H22C H 0.5244 0.3252 0.0620 0.064 Uiso 1 1 calc R . .
O30 O 0.31040(14) 0.03049(16) 0.11700(14) 0.0525(5) Uani 1 1 d . . .
C31 C 0.1906(3) 0.0622(4) 0.0429(3) 0.1014(15) Uani 1 1 d . . .
H31A H 0.1507 -0.0013 -0.0131 0.122 Uiso 1 1 calc R . .
H31B H 0.1937 0.1288 -0.0094 0.122 Uiso 1 1 calc R . .
C32 C 0.1222(3) 0.0899(4) 0.1250(3) 0.0907(12) Uani 1 1 d . . .
H32A H 0.0624 0.0292 0.1229 0.109 Uiso 1 1 calc R . .
H32B H 0.0776 0.1624 0.0994 0.109 Uiso 1 1 calc R . .
C33 C 0.2135(3) 0.1001(3) 0.2524(3) 0.0738(9) Uani 1 1 d . . .
H33A H 0.2358 0.1806 0.2736 0.089 Uiso 1 1 calc R . .
H33B H 0.1816 0.0674 0.3161 0.089 Uiso 1 1 calc R . .
C34 C 0.3189(3) 0.0347(3) 0.2444(2) 0.0663(8) Uani 1 1 d . . .
H34A H 0.3961 0.0720 0.2944 0.080 Uiso 1 1 calc R . .
H34B H 0.3176 -0.0432 0.2771 0.080 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'
Li Li -0.0003 0.0001 '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'
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
_geom_angle_publ_flag
O30 Li1 N1 108.61(18) . 3_655 ?
O30 Li1 C8 116.30(17) . . ?
N1 Li1 C8 116.14(17) 3_655 . ?
O30 Li1 C8 112.49(17) . 3_655 ?
N1 Li1 C8 82.04(14) 3_655 3_655 ?
C8 Li1 C8 116.38(15) . 3_655 ?
O30 Li1 Li1 141.5(3) . 3_655 ?
N1 Li1 Li1 106.5(2) 3_655 3_655 ?
C8 Li1 Li1 58.53(15) . 3_655 ?
C8 Li1 Li1 57.86(15) 3_655 3_655 ?
O30 Li1 C7 107.21(15) . . ?
N1 Li1 C7 95.45(14) 3_655 . ?
C8 Li1 C7 30.25(8) . . ?
C8 Li1 C7 138.87(16) 3_655 . ?
Li1 Li1 C7 84.29(18) 3_655 . ?
O30 Li1 C1 96.97(15) . 3_655 ?
N1 Li1 C1 30.98(8) 3_655 3_655 ?
C8 Li1 C1 142.76(17) . 3_655 ?
C8 Li1 C1 59.14(10) 3_655 3_655 ?
Li1 Li1 C1 105.3(2) 3_655 3_655 ?
C7 Li1 C1 126.41(15) . 3_655 ?
C1 N1 C21 113.88(17) . . ?
C1 N1 C22 111.01(15) . . ?
C21 N1 C22 109.24(18) . . ?
C1 N1 Li1 100.58(15) . 3_655 ?
C21 N1 Li1 114.81(16) . 3_655 ?
C22 N1 Li1 106.91(16) . 3_655 ?
C2 C1 C9 121.1(2) . . ?
C2 C1 N1 121.6(2) . . ?
C9 C1 N1 117.27(17) . . ?
C2 C1 Li1 149.33(16) . 3_655 ?
C9 C1 Li1 76.42(14) . 3_655 ?
N1 C1 Li1 48.44(12) . 3_655 ?
C1 C2 C3 120.8(2) . . ?
C4 C3 C2 120.2(2) . . ?
C3 C4 C10 121.1(2) . . ?
C6 C5 C10 120.5(2) . . ?
C5 C6 C7 119.6(2) . . ?
C8 C7 C6 125.4(2) . . ?
C8 C7 Li1 53.15(13) . . ?
C6 C7 Li1 168.80(18) . . ?
C7 C8 C9 113.35(18) . . ?
C7 C8 Li1 96.61(17) . . ?
C9 C8 Li1 147.02(18) . . ?
C7 C8 Li1 141.20(18) . 3_655 ?
C9 C8 Li1 97.15(16) . 3_655 ?
Li1 C8 Li1 63.62(15) . 3_655 ?
C1 C9 C10 116.58(19) . . ?
C1 C9 C8 120.87(18) . . ?
C10 C9 C8 122.54(19) . . ?
C5 C10 C4 121.5(2) . . ?
C5 C10 C9 118.4(2) . . ?
C4 C10 C9 120.1(2) . . ?
C31 O30 C34 108.7(2) . . ?
C31 O30 Li1 123.99(18) . . ?
C34 O30 Li1 126.74(18) . . ?
O30 C31 C32 108.5(3) . . ?
C31 C32 C33 106.1(2) . . ?
C34 C33 C32 103.8(2) . . ?
O30 C34 C33 107.5(2) . . ?
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 O30 1.932(4) . ?
Li1 N1 2.102(4) 3_655 ?
Li1 C8 2.207(4) . ?
Li1 C8 2.223(4) 3_655 ?
Li1 Li1 2.335(7) 3_655 ?
Li1 C7 2.740(4) . ?
Li1 C1 2.761(4) 3_655 ?
N1 C1 1.446(3) . ?
N1 C21 1.471(3) . ?
N1 C22 1.478(3) . ?
N1 Li1 2.102(4) 3_655 ?
C1 C2 1.375(3) . ?
C1 C9 1.436(3) . ?
C1 Li1 2.761(4) 3_655 ?
C2 C3 1.407(3) . ?
C3 C4 1.350(4) . ?
C4 C10 1.419(3) . ?
C5 C6 1.356(3) . ?
C5 C10 1.409(3) . ?
C6 C7 1.406(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.443(3) . ?
C8 Li1 2.223(4) 3_655 ?
C9 C10 1.435(3) . ?
O30 C31 1.415(3) . ?
O30 C34 1.414(3) . ?
C31 C32 1.444(4) . ?
C32 C33 1.486(4) . ?
C33 C34 1.471(4) . ?
