#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:41:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178663 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/74/4077492.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_4077492
loop_
_publ_author_name
'Nückel, Stefan'
'Burger, Peter'
_publ_section_title
;
 Transition Metal Complexes with Sterically Demanding Ligands.
 2.1Meisenheimer Complex Formation and Deprotonation Reactions of a
 Sterically Demanding Aromatic Diimine†
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              3305
_journal_paper_doi               10.1021/om000084k
_journal_volume                  19
_journal_year                    2000
_chemical_compound_source        synthesis
_chemical_formula_analytical     'C34 H42 Li2 N2 * 2 DME'
_chemical_formula_sum            'C42 H62 Li2 N2 O4'
_chemical_formula_weight         672.82
_chemical_melting_point          ?
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   'geom (a) and diference Fourier map (b)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 99.000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3560(10)
_cell_length_b                   14.8880(10)
_cell_length_c                   19.760(2)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      n/a
_cell_measurement_theta_min      n/a
_cell_volume                     4171.4(6)
_computing_cell_refinement       'STOE IPDS Programm Package'
_computing_data_collection       'STOE IPDS Programm Package'
_computing_data_reduction        'STOE IPDS Programm Package'
_computing_molecular_graphics    'Schakal97 (Keller, 1997)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device       'STOE IPDS'
_diffrn_measurement_method       'Image Plate'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7383
_diffrn_reflns_theta_max         25.87
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  n/a
_exptl_absorpt_correction_T_min  n/a
_exptl_absorpt_correction_type   n/a
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    n/a
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       n/a
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.068
_refine_ls_goodness_of_fit_obs   1.268
_refine_ls_hydrogen_treatment    'riding model (a), isotropic (b)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_restrained_S_obs      1.268
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_obs          0.0631
_refine_ls_shift/esd_max         0.813
_refine_ls_shift/esd_mean        0.030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+4.9321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1657
_refine_ls_wR_factor_obs         0.1551
_reflns_number_observed          2528
_reflns_number_total             3771
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            om000084k.cif
_cod_data_source_block           Complex5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'n/a' was changed to '?' - the value
is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+4.9321P] 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^)+(0.0500P)^2^+4.9321P] 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      I2/a
_cod_database_code               4077492
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.58312(14) 0.24114(13) 0.42115(10) 0.0436(5) Uani 1 d . .
Li1 Li 0.5737(3) 0.2267(4) 0.5156(2) 0.0620(13) Uani 1 d . .
C1 C 0.6910(2) 0.11948(14) 0.44786(13) 0.0369(5) Uani 1 d . .
C2 C 0.7500 0.1645(2) 0.5000 0.0341(7) Uani 1 d S .
C3 C 0.6924(2) 0.0262(2) 0.4487(2) 0.0550(7) Uani 1 d . .
H3 H 0.6544(2) -0.0058(2) 0.4146(2) 0.066 Uiso 1 calc R .
C4 C 0.7500 -0.0190(3) 0.5000 0.0707(13) Uani 1 d S .
H4 H 0.7500 -0.0814(3) 0.5000 0.085 Uiso 1 calc SR .
C5 C 0.6288(2) 0.1726(2) 0.39407(13) 0.0396(6) Uani 1 d . .
C6 C 0.6263(2) 0.1489(2) 0.3277(2) 0.0596(8) Uani 1 d . .
H6 H 0.5827(20) 0.1824(19) 0.2899(16) 0.064(8) Uiso 1 d . .
H6A H 0.6687(19) 0.0982(19) 0.3160(14) 0.055(8) Uiso 1 d . .
C7 C 0.5346(2) 0.3037(2) 0.37387(12) 0.0402(6) Uani 1 d . .
C8 C 0.5834(2) 0.3752(2) 0.34838(13) 0.0450(6) Uani 1 d . .
C9 C 0.5332(2) 0.4386(2) 0.30536(13) 0.0482(6) Uani 1 d . .
H9 H 0.5655(2) 0.4855(2) 0.28841(13) 0.058 Uiso 1 calc R .
C10 C 0.4367(2) 0.4334(2) 0.28737(14) 0.0527(7) Uani 1 d . .
H10 H 0.4043(2) 0.4764(2) 0.25873(14) 0.063 Uiso 1 calc R .
C11 C 0.3890(2) 0.3641(2) 0.3121(2) 0.0583(8) Uani 1 d . .
H11 H 0.3238(2) 0.3610(2) 0.3002(2) 0.070 Uiso 1 calc R .
C12 C 0.4358(2) 0.2981(2) 0.35481(14) 0.0494(7) Uani 1 d . .
C13 C 0.6894(2) 0.3862(2) 0.3684(2) 0.0604(8) Uani 1 d . .
H13 H 0.7147(2) 0.3400(2) 0.4017(2) 0.073 Uiso 1 calc R 5
C14 C 0.7161(5) 0.4860(9) 0.3991(7) 0.082(3) Uani 0.67(3) d P 5
H14A H 0.6983(27) 0.5300(10) 0.3639(9) 0.123 Uiso 0.67(3) calc PR 5
H14B H 0.7828(7) 0.4895(13) 0.4145(21) 0.123 Uiso 0.67(3) calc PR 5
H14C H 0.6830(24) 0.4974(14) 0.4368(15) 0.123 Uiso 0.67(3) calc PR 5
C14A C 0.7135(9) 0.4343(29) 0.4256(15) 0.089(9) Uani 0.33(3) d P 6
H14D H 0.7802(14) 0.4294(65) 0.4405(34) 0.134 Uiso 0.33(3) calc PR 6
H14E H 0.6804(55) 0.4120(50) 0.4607(20) 0.134 Uiso 0.33(3) calc PR 6
H14F H 0.6971(66) 0.4961(30) 0.4165(19) 0.134 Uiso 0.33(3) calc PR 6
C15 C 0.7398(2) 0.3841(3) 0.3071(2) 0.0863(11) Uani 1 d . .
H15A H 0.7229(14) 0.4362(9) 0.2793(7) 0.130 Uiso 1 calc R .
H15B H 0.7219(14) 0.3310(9) 0.2807(8) 0.130 Uiso 1 calc R .
H15C H 0.8067(2) 0.3837(18) 0.3221(2) 0.130 Uiso 1 calc R .
C16 C 0.3802(2) 0.2215(2) 0.3802(2) 0.0729(10) Uani 1 d . .
H16 H 0.4288(2) 0.1802(2) 0.4023(2) 0.088 Uiso 1 calc R 2
C17 C 0.3666(9) 0.1482(10) 0.3264(10) 0.110(4) Uani 0.56(2) d P 7
H17A H 0.4258(12) 0.1192(31) 0.3246(26) 0.166 Uiso 0.56(2) calc PR 7
H17B H 0.3432(45) 0.1741(11) 0.2825(11) 0.166 Uiso 0.56(2) calc PR 7
H17C H 0.3220(36) 0.1050(24) 0.3380(20) 0.166 Uiso 0.56(2) calc PR 7
C18 C 0.2762(8) 0.2541(7) 0.3916(9) 0.104(5) Uani 0.56(2) d P 7
H18A H 0.2436(19) 0.2049(13) 0.4089(32) 0.155 Uiso 0.56(2) calc PR 7
H18B H 0.2414(17) 0.2739(40) 0.3488(11) 0.155 Uiso 0.56(2) calc PR 7
H18C H 0.2820(8) 0.3026(28) 0.4240(25) 0.155 Uiso 0.56(2) calc PR 7
C17A C 0.3241(14) 0.1659(13) 0.3243(9) 0.097(5) Uani 0.44(2) d P 2
H17D H 0.3615(24) 0.1548(46) 0.2889(21) 0.145 Uiso 0.44(2) calc PR 2
H17E H 0.2679(30) 0.1978(25) 0.3054(28) 0.145 Uiso 0.44(2) calc PR 2
H17F H 0.3073(48) 0.1098(24) 0.3430(12) 0.145 Uiso 0.44(2) calc PR 2
C18A C 0.3319(17) 0.2508(10) 0.4355(10) 0.116(7) Uani 0.44(2) d P 2
H18D H 0.2980(52) 0.3053(33) 0.4224(20) 0.174 Uiso 0.44(2) calc PR 2
H18E H 0.3772(18) 0.2615(58) 0.4758(16) 0.174 Uiso 0.44(2) calc PR 2
H18F H 0.2884(49) 0.2052(26) 0.4448(33) 0.174 Uiso 0.44(2) calc PR 2
O1 O 0.5470(7) 0.3312(8) 0.5716(5) 0.054(2) Uani 0.69(3) d P 3
O2 O 0.5381(14) 0.1569(10) 0.5912(10) 0.060(3) Uani 0.69(3) d P 3
C19 C 0.5137(9) 0.4114(10) 0.5434(6) 0.069(2) Uani 0.69(3) d P 3
H19A H 0.5451(22) 0.4255(18) 0.5052(14) 0.104 Uiso 0.69(3) calc PR 3
H19B H 0.5257(28) 0.4581(10) 0.5772(9) 0.104 Uiso 0.69(3) calc PR 3
H19C H 0.4471(10) 0.4068(12) 0.5280(20) 0.104 Uiso 0.69(3) calc PR 3
C20 C 0.5009(8) 0.3012(9) 0.6266(5) 0.062(2) Uani 0.69(3) d P 3
H20A H 0.4339(8) 0.2941(9) 0.6108(5) 0.075 Uiso 0.69(3) calc PR 3
H20B H 0.5094(8) 0.3448(9) 0.6635(5) 0.075 Uiso 0.69(3) calc PR 3
C21 C 0.5433(7) 0.2132(8) 0.6515(6) 0.062(2) Uani 0.69(3) d P 3
H21A H 0.6084(7) 0.2210(8) 0.6729(6) 0.074 Uiso 0.69(3) calc PR 3
H21B H 0.5082(7) 0.1865(8) 0.6845(6) 0.074 Uiso 0.69(3) calc PR 3
C22 C 0.5708(7) 0.0660(10) 0.6076(5) 0.065(3) Uani 0.69(3) d P 3
H22A H 0.5716(24) 0.0329(12) 0.5660(5) 0.097 Uiso 0.69(3) calc PR 3
H22B H 0.5291(15) 0.0370(12) 0.6343(16) 0.097 Uiso 0.69(3) calc PR 3
H22C H 0.6333(11) 0.0678(10) 0.6334(15) 0.097 Uiso 0.69(3) calc PR 3
O1A O 0.5265(22) 0.3015(16) 0.5692(13) 0.068(5) Uani 0.31(3) d P 4
O2A O 0.5367(29) 0.1300(26) 0.5828(26) 0.067(7) Uani 0.31(3) d P 4
C19A C 0.4836(36) 0.3944(32) 0.5425(22) 0.141(16) Uani 0.31(3) d P 4
H19D H 0.5175(87) 0.4172(65) 0.5080(65) 0.212 Uiso 0.31(3) calc PR 4
H19E H 0.4885(113) 0.4361(44) 0.5799(27) 0.212 Uiso 0.31(3) calc PR 4
H19F H 0.4184(50) 0.3866(36) 0.5233(84) 0.212 Uiso 0.31(3) calc PR 4
C20A C 0.4787(27) 0.2655(26) 0.6195(18) 0.095(8) Uani 0.31(3) d P 4
H20C H 0.4131(27) 0.2537(26) 0.6014(18) 0.114 Uiso 0.31(3) calc PR 4
H20D H 0.4821(27) 0.3053(26) 0.6587(18) 0.114 Uiso 0.31(3) calc PR 4
C21A C 0.5309(24) 0.1811(25) 0.6380(18) 0.099(10) Uani 0.31(3) d P 4
H21C H 0.5941(24) 0.1954(25) 0.6607(18) 0.119 Uiso 0.31(3) calc PR 4
H21D H 0.4995(24) 0.1475(25) 0.6699(18) 0.119 Uiso 0.31(3) calc PR 4
C22A C 0.5720(28) 0.0419(25) 0.6020(22) 0.162(20) Uani 0.31(3) d P 4
H22D H 0.5508(76) 0.0003(19) 0.5657(35) 0.243 Uiso 0.31(3) calc PR 4
H22E H 0.5491(73) 0.0233(54) 0.6430(42) 0.243 Uiso 0.31(3) calc PR 4
H22F H 0.6397(28) 0.0431(19) 0.6102(62) 0.243 Uiso 0.31(3) calc PR 4
H2 H 0.7536(44) 0.2327(22) 0.5051(58) 0.038(9) Uiso 0.50 d PR 4
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
C5 N1 C7 116.6(2) . .
C5 N1 Li1 114.3(2) . .
C7 N1 Li1 128.0(2) . .
O1A Li1 N1 128.1(8) . .
N1 Li1 O2 151.3(5) . .
N1 Li1 O1 120.6(4) . .
O2 Li1 O1 83.9(5) . .
O1A Li1 O2A 83.8(10) . .
N1 Li1 O2A 140.0(13) . .
O1A Li1 C21A 56.4(9) . .
N1 Li1 C21A 167.5(9) . .
O2A Li1 C21A 29.6(10) . .
O1A Li1 C20A 27.3(7) . .
N1 Li1 C20A 147.5(8) . .
O2A Li1 C20A 56.9(10) . .
C21A Li1 C20A 31.9(9) . .
O1A Li1 C2 137.1(11) . .
N1 Li1 C2 73.8(2) . .
O2 Li1 C2 105.2(6) . .
O1 Li1 C2 126.0(4) . .
O2A Li1 C2 99.7(11) . .
C21A Li1 C2 111.1(7) . .
C20A Li1 C2 137.6(9) . .
O1A Li1 C5 154.8(7) . .
N1 Li1 C5 26.79(11) . .
O2 Li1 C5 130.9(5) . .
O1 Li1 C5 145.2(4) . .
O2A Li1 C5 119.2(11) . .
C21A Li1 C5 148.1(8) . .
C20A Li1 C5 166.1(10) . .
C2 Li1 C5 54.02(10) . .
C3 C1 C2 117.7(2) . .
C3 C1 C5 122.7(2) . .
C2 C1 C5 119.6(2) . .
C1 C2 C1 122.7(3) . 2_656
C1 C2 Li1 122.64(13) . 2_656
C1 C2 Li1 77.46(15) 2_656 2_656
C1 C2 Li1 77.46(15) . .
C1 C2 Li1 122.64(13) 2_656 .
Li1 C2 Li1 140.7(3) 2_656 .
C4 C3 C1 120.2(3) . .
C3 C4 C3 121.6(4) 2_656 .
C6 C5 N1 129.3(2) . .
C6 C5 C1 118.1(2) . .
N1 C5 C1 112.6(2) . .
C6 C5 Li1 161.9(2) . .
N1 C5 Li1 38.92(15) . .
C1 C5 Li1 76.0(2) . .
C8 C7 C12 119.0(2) . .
C8 C7 N1 120.6(2) . .
C12 C7 N1 120.3(2) . .
C9 C8 C7 119.4(2) . .
C9 C8 C13 119.2(2) . .
C7 C8 C13 121.4(2) . .
C10 C9 C8 121.5(2) . .
C11 C10 C9 119.3(2) . .
C10 C11 C12 121.7(3) . .
C11 C12 C7 119.2(2) . .
C11 C12 C16 119.9(2) . .
C7 C12 C16 120.9(2) . .
C14A C13 C15 126.7(13) . .
C14A C13 C8 113.3(6) . .
C15 C13 C8 112.0(3) . .
C15 C13 C14 101.7(6) . .
C8 C13 C14 111.3(3) . .
C18A C16 C17A 117.0(8) . .
C18A C16 C12 111.1(5) . .
C17A C16 C12 114.6(8) . .
C17 C16 C12 109.0(6) . .
C17 C16 C18 107.1(6) . .
C12 C16 C18 111.4(4) . .
C19 O1 C20 114.1(9) . .
C19 O1 Li1 122.8(8) . .
C20 O1 Li1 109.4(6) . .
C21 O2 C22 112.4(15) . .
C21 O2 Li1 109.6(10) . .
C22 O2 Li1 123.6(11) . .
O1 C20 C21 108.1(9) . .
O2 C21 C20 105.7(11) . .
C20A O1A C19A 111.4(24) . .
C20A O1A Li1 117.9(13) . .
C19A O1A Li1 121.8(21) . .
C21A O2A C22A 111.5(39) . .
C21A O2A Li1 100.3(22) . .
C22A O2A Li1 133.3(27) . .
O1A C20A C21A 102.3(24) . .
O1A C20A Li1 34.8(10) . .
C21A C20A Li1 73.0(16) . .
O2A C21A C20A 112.0(29) . .
O2A C21A Li1 50.0(19) . .
C20A C21A Li1 75.0(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.366(3) .
N1 C7 1.422(3) .
N1 Li1 1.904(5) .
Li1 O1A 1.74(2) .
Li1 O2 1.95(2) .
Li1 O1 1.981(12) .
Li1 O2A 2.08(4) .
Li1 C21A 2.67(3) .
Li1 C20A 2.70(3) .
Li1 C2 2.757(5) .
Li1 C5 2.763(5) .
C1 C3 1.389(3) .
C1 C2 1.398(3) .
C1 C5 1.502(3) .
C2 C1 1.398(3) 2_656
C2 Li1 2.757(5) 2_656
C3 C4 1.379(3) .
C4 C3 1.379(3) 2_656
C5 C6 1.353(4) .
C7 C8 1.410(3) .
C7 C12 1.411(3) .
C8 C9 1.394(4) .
C8 C13 1.520(4) .
C9 C10 1.377(4) .
C10 C11 1.370(4) .
C11 C12 1.397(4) .
C12 C16 1.522(4) .
C13 C14A 1.336(15) .
C13 C15 1.507(4) .
C13 C14 1.628(11) .
C16 C18A 1.450(13) .
C16 C17A 1.51(2) .
C16 C17 1.51(2) .
C16 C18 1.618(9) .
O1 C19 1.37(2) .
O1 C20 1.428(13) .
O2 C21 1.448(14) .
O2 C22 1.45(2) .
C20 C21 1.50(2) .
O1A C20A 1.40(3) .
O1A C19A 1.57(5) .
O2A C21A 1.34(3) .
O2A C22A 1.44(5) .
C20A C21A 1.48(4) .
