#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:38:32 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178526 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/31/4063194.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_4063194
loop_
_publ_author_name
'Johannes Belzner'
'Dirk Schär'
'Uwe Dehnert'
'Mathias Noltemeyer'
_publ_section_title
;
 Synthesis and Structure of Aryllithium Compounds Containing
 ortho-Directing (Dimethylamino)methyl and Trimethylhydrazino
 Substituents
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              285
_journal_page_last               288
_journal_paper_doi               10.1021/om960858q
_journal_volume                  16
_journal_year                    1997
_chemical_formula_sum            'C24 H42 Li2 N6'
_chemical_formula_weight         428.52
_chemical_name_common            6
_chemical_name_systematic
; 
 (2-(trimethylhydrazino)phenyl lithium)2 TMEDA 
;
_chemical_temperature_decomposition 438.15
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.22(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.106(2)
_cell_length_b                   13.654(3)
_cell_length_c                   17.189(3)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     2666.2(9)
_computing_cell_refinement       'Stoe Dif4'
_computing_data_collection       'Stoe Dif4'
_computing_data_reduction        'Stoe Redu4'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measurement_device       'Stoe AED2'
_diffrn_measurement_method       'profile fitting'
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3052
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         3.59
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            none
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_description       plates
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.034
_refine_ls_goodness_of_fit_obs   1.059
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_restrained_S_obs      1.059
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_obs          0.0619
_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/[σ²(Fo²)+(0.0800P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1794
_refine_ls_wR_factor_obs         0.1556
_reflns_number_observed          1352
_reflns_number_total             1732
_reflns_observed_criterion       >2sigma(I)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as 'dec. 165 \%C'. The value 'dec. 165 \%C' was changed to '438.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+4.0000P] 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^)+(0.0800P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4063194
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Li1 Li 0.0000 0.6045(4) 0.2500 0.0375(14) Uani 1 d S
Li2 Li 0.0000 0.7798(4) 0.2500 0.0363(14) Uani 1 d S
N1 N 0.0358(2) 0.4863(2) 0.33987(14) 0.0432(6) Uani 1 d .
N2 N -0.0042(2) 0.7730(2) 0.08532(13) 0.0424(7) Uani 1 d .
N3 N -0.0432(2) 0.8432(2) 0.13361(14) 0.0437(7) Uani 1 d .
C1 C 0.1279(2) 0.7036(2) 0.2155(2) 0.0351(7) Uani 1 d .
C2 C 0.1085(2) 0.7316(2) 0.1322(2) 0.0358(7) Uani 1 d .
C3 C 0.1910(3) 0.7161(2) 0.0934(2) 0.0497(8) Uani 1 d .
H3A H 0.1730(3) 0.7358(2) 0.0367(2) 0.075 Uiso 1 d R
C4 C 0.2975(3) 0.6726(2) 0.1362(2) 0.0627(10) Uani 1 d .
H4A H 0.3531(3) 0.6600(2) 0.1089(2) 0.094 Uiso 1 d R
C5 C 0.3241(3) 0.6474(2) 0.2181(2) 0.0587(9) Uani 1 d .
H5A H 0.3993(3) 0.6197(2) 0.2493(2) 0.088 Uiso 1 d R
C6 C 0.2400(2) 0.6635(2) 0.2558(2) 0.0439(8) Uani 1 d .
H6A H 0.2595(2) 0.6456(2) 0.3130(2) 0.066 Uiso 1 d R
C7 C -0.0213(4) 0.8062(3) 0.0005(2) 0.0674(10) Uani 1 d .
H7A H -0.0162(22) 0.7499(4) -0.0335(4) 0.101 Uiso 1 calc R
H7B H 0.0399(13) 0.8538(14) 0.0019(2) 0.101 Uiso 1 calc R
H7C H -0.0989(9) 0.8368(16) -0.0234(6) 0.101 Uiso 1 calc R
C8 C -0.1719(3) 0.8485(4) 0.1034(2) 0.0862(14) Uani 1 d .
H8A H -0.1998(3) 0.8803(20) 0.0490(9) 0.129 Uiso 1 calc R
H8B H -0.1975(3) 0.8866(18) 0.1425(10) 0.129 Uiso 1 calc R
H8C H -0.2047(3) 0.7822(4) 0.0987(17) 0.129 Uiso 1 calc R
C9 C 0.0105(4) 0.9394(2) 0.1353(2) 0.0710(11) Uani 1 d .
H9A H -0.0189(17) 0.9682(8) 0.0796(4) 0.107 Uiso 1 calc R
H9B H 0.0962(4) 0.9324(3) 0.1532(15) 0.107 Uiso 1 calc R
H9C H -0.0099(18) 0.9821(6) 0.1741(12) 0.107 Uiso 1 calc R
C10 C 0.0353(5) 0.3989(3) 0.2928(2) 0.098(2) Uani 1 d .
H10A H 0.1175(5) 0.3851(3) 0.2971(2) 0.147 Uiso 1 calc R
H10B H 0.0091(5) 0.3439(3) 0.3196(2) 0.147 Uiso 1 calc R
C11 C 0.1465(4) 0.4968(4) 0.4075(3) 0.115(2) Uani 1 d .
H11A H 0.1546(17) 0.4440(18) 0.4477(13) 0.172 Uiso 1 calc R
H11B H 0.1483(14) 0.5602(13) 0.4347(15) 0.172 Uiso 1 calc R
H11C H 0.2115(4) 0.4934(29) 0.3860(5) 0.172 Uiso 1 calc R
C12 C -0.0571(4) 0.4806(3) 0.3755(3) 0.098(2) Uani 1 d .
H12A H -0.0471(18) 0.4210(13) 0.4089(17) 0.147 Uiso 1 calc R
H12B H -0.1339(4) 0.4791(24) 0.3308(3) 0.147 Uiso 1 calc R
H12C H -0.0529(18) 0.5380(13) 0.4106(16) 0.147 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 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'
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
N1 Li1 N1 84.0(2) 2 .
N1 Li1 C1 104.01(9) 2 .
N1 Li1 C1 129.67(11) . .
N1 Li1 C1 129.67(11) 2 2
N1 Li1 C1 104.01(9) . 2
C1 Li1 C1 107.4(3) . 2
N1 Li1 Li2 138.02(12) 2 .
N1 Li1 Li2 138.02(12) . .
C1 Li1 Li2 53.68(14) . .
C1 Li1 Li2 53.68(14) 2 .
N3 Li2 N3 130.7(3) 2 .
N3 Li2 C1 120.75(10) 2 .
N3 Li2 C1 84.20(10) . .
N3 Li2 C1 84.20(10) 2 2
N3 Li2 C1 120.75(10) . 2
C1 Li2 C1 121.0(3) . 2
N3 Li2 Li1 114.6(2) 2 .
N3 Li2 Li1 114.6(2) . .
C1 Li2 Li1 60.5(2) . .
C1 Li2 Li1 60.5(2) 2 .
C10 N1 C11 110.9(3) . .
C10 N1 C12 109.8(3) . .
C11 N1 C12 107.6(3) . .
C10 N1 Li1 104.8(2) . .
C11 N1 Li1 113.6(2) . .
C12 N1 Li1 110.2(2) . .
C2 N2 N3 111.9(2) . .
C2 N2 C7 117.2(2) . .
N3 N2 C7 113.7(2) . .
N2 N3 C9 112.0(2) . .
N2 N3 C8 110.4(3) . .
C9 N3 C8 111.9(3) . .
N2 N3 Li2 104.7(2) . .
C9 N3 Li2 113.2(2) . .
C8 N3 Li2 104.2(2) . .
C6 C1 C2 113.4(2) . .
C6 C1 Li2 136.9(2) . .
C2 C1 Li2 105.6(2) . .
C6 C1 Li1 105.5(2) . .
C2 C1 Li1 122.0(2) . .
Li2 C1 Li1 65.8(2) . .
C3 C2 C1 123.0(3) . .
C3 C2 N2 119.3(2) . .
C1 C2 N2 117.7(2) . .
C4 C3 C2 120.1(3) . .
C5 C4 C3 119.9(3) . .
C4 C5 C6 119.0(3) . .
C5 C6 C1 124.4(3) . .
C10 C10 N1 117.7(3) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li1 N1 2.172(5) 2
Li1 N1 2.172(5) .
Li1 C1 2.284(4) .
Li1 C1 2.284(4) 2
Li1 Li2 2.393(9) .
Li2 N3 2.074(3) 2
Li2 N3 2.074(3) .
Li2 C1 2.114(4) .
Li2 C1 2.114(4) 2
N1 C10 1.440(4) .
N1 C11 1.445(4) .
N1 C12 1.457(4) .
N2 C2 1.439(4) .
N2 N3 1.449(3) .
N2 C7 1.471(4) .
N3 C9 1.462(4) .
N3 C8 1.465(4) .
C1 C6 1.405(4) .
C1 C2 1.420(4) .
C2 C3 1.395(4) .
C3 C4 1.379(5) .
C4 C5 1.375(5) .
C5 C6 1.399(4) .
C10 C10 1.422(7) 2
