# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb211ds
_database_code_depnum_ccdc_archive 'CCDC 1472608'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H44 Li2 N2 O2'
_chemical_formula_sum            'C34 H44 Li2 N2 O2'
_chemical_formula_weight         526.59

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9155(5)
_cell_length_b                   9.4118(8)
_cell_length_c                   10.9072(9)
_cell_angle_alpha                92.056(5)
_cell_angle_beta                 96.772(4)
_cell_angle_gamma                108.294(4)
_cell_volume                     763.83(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    23211
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.17

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_process_details   'SABABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23211
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.79
_reflns_number_total             3965
_reflns_number_gt                2656
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'Bruker Saint'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    XSeed
_computing_publication_material  CIF_TAB

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0824P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3965
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1355
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.29921(13) 0.60638(11) 0.77318(9) 0.0230(3) Uani 1 1 d . . .
N1 N 0.41539(14) 0.59425(12) 1.08878(10) 0.0165(3) Uani 1 1 d . . .
C1 C 0.48940(17) 0.70098(14) 1.18642(12) 0.0157(3) Uani 1 1 d . . .
C2 C 0.39649(18) 0.73377(15) 1.27977(13) 0.0195(3) Uani 1 1 d . . .
H2 H 0.2706 0.6854 1.2736 0.023 Uiso 1 1 calc R . .
C3 C 0.4837(2) 0.83555(16) 1.38172(13) 0.0226(3) Uani 1 1 d . . .
H3 H 0.4149 0.8545 1.4423 0.027 Uiso 1 1 calc R . .
C4 C 0.66426(19) 0.90847(16) 1.39708(13) 0.0224(3) Uani 1 1 d . . .
H4 H 0.7210 0.9736 1.4690 0.027 Uiso 1 1 calc R . .
C5 C 0.76569(18) 0.88551(15) 1.30415(13) 0.0194(3) Uani 1 1 d . . .
C6 C 0.95240(19) 0.96084(16) 1.31382(14) 0.0260(3) Uani 1 1 d . . .
H6 H 1.0115 1.0252 1.3857 0.031 Uiso 1 1 calc R . .
C7 C 1.0503(2) 0.94355(17) 1.22250(15) 0.0288(4) Uani 1 1 d . . .
H7 H 1.1764 0.9923 1.2326 0.035 Uiso 1 1 calc R . .
C8 C 0.96349(19) 0.85359(16) 1.11400(15) 0.0258(3) Uani 1 1 d . . .
H8 H 1.0298 0.8452 1.0485 0.031 Uiso 1 1 calc R . .
C9 C 0.78353(18) 0.77793(15) 1.10224(13) 0.0197(3) Uani 1 1 d . . .
H9 H 0.7267 0.7174 1.0280 0.024 Uiso 1 1 calc R . .
C10 C 0.67891(17) 0.78698(14) 1.19734(12) 0.0166(3) Uani 1 1 d . . .
C11 C 0.22017(18) 0.53123(16) 1.07690(13) 0.0216(3) Uani 1 1 d . . .
H11A H 0.1745 0.4952 0.9891 0.026 Uiso 1 1 calc R . .
H11B H 0.1719 0.6131 1.0971 0.026 Uiso 1 1 calc R . .
C12 C 0.1453(2) 0.40451(16) 1.15571(14) 0.0259(3) Uani 1 1 d . . .
H12 H 0.0196 0.3540 1.1402 0.031 Uiso 1 1 calc R . .
C13 C 0.2375(2) 0.35710(16) 1.24401(14) 0.0289(4) Uani 1 1 d . . .
H13A H 0.3636 0.4041 1.2629 0.035 Uiso 1 1 calc R . .
H13B H 0.1780 0.2758 1.2889 0.035 Uiso 1 1 calc R . .
C14 C 0.3402(2) 0.75999(16) 0.74283(14) 0.0283(4) Uani 1 1 d . . .
H14A H 0.2279 0.7813 0.7140 0.034 Uiso 1 1 calc R . .
H14B H 0.4162 0.7779 0.6754 0.034 Uiso 1 1 calc R . .
C15 C 0.4372(2) 0.86086(17) 0.85539(15) 0.0327(4) Uani 1 1 d . . .
H15A H 0.3630 0.8401 0.9226 0.049 Uiso 1 1 calc R . .
H15B H 0.4611 0.9658 0.8364 0.049 Uiso 1 1 calc R . .
H15C H 0.5512 0.8428 0.8810 0.049 Uiso 1 1 calc R . .
C16 C 0.1747(2) 0.50050(17) 0.67908(14) 0.0281(4) Uani 1 1 d . . .
H16A H 0.0758 0.5398 0.6505 0.034 Uiso 1 1 calc R . .
H16B H 0.1218 0.4047 0.7161 0.034 Uiso 1 1 calc R . .
C17 C 0.2600(2) 0.47029(19) 0.56938(15) 0.0374(4) Uani 1 1 d . . .
H17A H 0.3052 0.5632 0.5286 0.056 Uiso 1 1 calc R . .
H17B H 0.1707 0.3945 0.5109 0.056 Uiso 1 1 calc R . .
H17C H 0.3599 0.4334 0.5971 0.056 Uiso 1 1 calc R . .
Li1 Li 0.4399(3) 0.5552(3) 0.9103(2) 0.0233(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
O1 C14 1.4388(17) . ?
O1 C16 1.4454(18) . ?
O1 Li1 1.924(2) . ?
N1 C1 1.3759(16) . ?
N1 C11 1.4589(17) . ?
N1 Li1 2.012(3) . ?
N1 Li1 2.074(3) 2_667 ?
C1 C2 1.4033(18) . ?
C1 C10 1.4520(18) . ?
C2 C3 1.3993(19) . ?
C3 C4 1.3643(19) . ?
C4 C5 1.4155(19) . ?
C5 C6 1.4135(19) . ?
C5 C10 1.4223(19) . ?
C6 C7 1.367(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.3661(19) . ?
C9 C10 1.4176(18) . ?
C11 C12 1.504(2) . ?
C11 Li1 2.628(3) . ?
C12 C13 1.315(2) . ?
C14 C15 1.495(2) . ?
C16 C17 1.502(2) . ?
Li1 N1 2.074(3) 2_667 ?
Li1 Li1 2.479(5) 2_667 ?

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
C14 O1 C16 113.51(11) . . ?
C14 O1 Li1 119.98(11) . . ?
C16 O1 Li1 125.33(11) . . ?
C1 N1 C11 113.87(10) . . ?
C1 N1 Li1 140.27(11) . . ?
C11 N1 Li1 97.17(10) . . ?
C1 N1 Li1 108.90(10) . 2_667 ?
C11 N1 Li1 117.42(10) . 2_667 ?
Li1 N1 Li1 74.70(11) . 2_667 ?
N1 C1 C2 125.17(12) . . ?
N1 C1 C10 118.88(11) . . ?
C2 C1 C10 115.94(12) . . ?
C3 C2 C1 122.00(13) . . ?
C4 C3 C2 122.21(13) . . ?
C3 C4 C5 118.95(13) . . ?
C6 C5 C4 121.36(13) . . ?
C6 C5 C10 118.78(13) . . ?
C4 C5 C10 119.85(12) . . ?
C7 C6 C5 121.77(14) . . ?
C6 C7 C8 119.61(14) . . ?
C9 C8 C7 120.05(14) . . ?
C8 C9 C10 122.04(13) . . ?
C9 C10 C5 117.56(12) . . ?
C9 C10 C1 121.71(12) . . ?
C5 C10 C1 120.72(12) . . ?
N1 C11 C12 116.61(11) . . ?
N1 C11 Li1 49.41(8) . . ?
C12 C11 Li1 130.30(11) . . ?
C13 C12 C11 126.14(13) . . ?
O1 C14 C15 109.01(12) . . ?
O1 C16 C17 113.30(13) . . ?
O1 Li1 N1 123.79(12) . . ?
O1 Li1 N1 128.90(13) . 2_667 ?
N1 Li1 N1 105.30(11) . 2_667 ?
O1 Li1 Li1 167.60(19) . 2_667 ?
N1 Li1 Li1 53.80(9) . 2_667 ?
N1 Li1 Li1 51.51(9) 2_667 2_667 ?
O1 Li1 C11 99.30(10) . . ?
N1 Li1 C11 33.42(6) . . ?
N1 Li1 C11 117.23(11) 2_667 . ?
Li1 Li1 C11 72.87(11) 2_667 . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb227jga
_database_code_depnum_ccdc_archive 'CCDC 1472609'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H56 Li2 N6'
_chemical_formula_sum            'C38 H56 Li2 N6'
_chemical_formula_weight         610.77

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   9.170(3)
_cell_length_b                   24.337(9)
_cell_length_c                   33.568(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7492(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3228
_cell_measurement_theta_min      7.59
_cell_measurement_theta_max      23.14

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2656
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15289
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.92
_reflns_number_total             3937
_reflns_number_gt                2901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    XSeed
_computing_publication_material  CIF-TAB

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The molecule of TMEDA was dissordered with its backbone C16 C17 modelled over
two positions and restrained
;

_vrf_DIFMX01_vb227jga            
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: The complex is composed of light atoms and the data:parameter ratio
is poor due to this.
;
_vrf_PLAT097_vb227jga            
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.86 eA-3  
RESPONSE: The residual electron density is closest to C2 at 1.416 angstroms.
It lies in a non chemically sensible place.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1616P)²+9.5072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(5)
_refine_ls_number_reflns         3937
_refine_ls_number_parameters     231
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.2657
_refine_ls_wR_factor_gt          0.2389
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.5557(4) 0.07649(15) 0.29886(12) 0.0600(9) Uani 1 1 d . . .
N2 N 0.6708(3) 0.04297(13) 0.44729(10) 0.0484(8) Uani 1 1 d . . .
N3 N 0.6635(3) -0.04684(15) 0.50485(11) 0.0567(9) Uani 1 1 d . . .
C1 C 0.8292(13) 0.0085(5) 0.2485(4) 0.160(4) Uani 1 1 d . . .
H1A H 0.8930 0.0078 0.2708 0.192 Uiso 1 1 calc R . .
H1B H 0.8444 -0.0160 0.2269 0.192 Uiso 1 1 calc R . .
C2 C 0.7236(7) 0.0421(3) 0.2476(2) 0.095(2) Uani 1 1 d . . .
H2 H 0.6595 0.0429 0.2254 0.114 Uiso 1 1 calc R . .
C3 C 0.7007(6) 0.0806(3) 0.2819(2) 0.098(2) Uani 1 1 d . . .
H3A H 0.7735 0.0725 0.3029 0.118 Uiso 1 1 calc R . .
H3B H 0.7171 0.1188 0.2728 0.118 Uiso 1 1 calc R . .
C4 C 0.5210(3) 0.11616(13) 0.32554(12) 0.0442(8) Uani 1 1 d . . .
C5 C 0.6105(5) 0.15851(16) 0.33846(16) 0.0633(12) Uani 1 1 d . . .
H5 H 0.7033 0.1632 0.3264 0.076 Uiso 1 1 calc R . .
C6 C 0.5666(6) 0.19550(18) 0.36966(17) 0.0756(15) Uani 1 1 d . . .
H6 H 0.6335 0.2228 0.3784 0.091 Uiso 1 1 calc R . .
C7 C 0.4334(7) 0.1930(2) 0.38712(16) 0.0771(14) Uani 1 1 d . . .
H7 H 0.4062 0.2183 0.4073 0.093 Uiso 1 1 calc R . .
C8 C 0.3381(5) 0.15237(18) 0.37464(12) 0.0591(10) Uani 1 1 d . . .
C9 C 0.1926(7) 0.1468(3) 0.39161(14) 0.0804(18) Uani 1 1 d . . .
H9 H 0.1657 0.1706 0.4129 0.097 Uiso 1 1 calc R . .
C10 C 0.0942(6) 0.1098(3) 0.37867(19) 0.0830(17) Uani 1 1 d . . .
H10 H -0.0012 0.1089 0.3897 0.100 Uiso 1 1 calc R . .
C11 C 0.1325(5) 0.0742(2) 0.35010(18) 0.0759(16) Uani 1 1 d . . .
H11 H 0.0640 0.0472 0.3418 0.091 Uiso 1 1 calc R . .
C12 C 0.2714(4) 0.07544(15) 0.33180(14) 0.0536(10) Uani 1 1 d . . .
H12 H 0.2936 0.0503 0.3110 0.064 Uiso 1 1 calc R . .
C13 C 0.3781(4) 0.11429(13) 0.34436(11) 0.0418(7) Uani 1 1 d . . .
C14 C 0.6818(7) 0.1023(2) 0.4533(2) 0.0882(18) Uani 1 1 d . A .
H14A H 0.6985 0.1100 0.4815 0.132 Uiso 1 1 calc R . .
H14B H 0.5910 0.1199 0.4447 0.132 Uiso 1 1 calc R . .
H14C H 0.7633 0.1167 0.4376 0.132 Uiso 1 1 calc R . .
C15 C 0.6663(6) 0.0338(3) 0.40501(18) 0.0823(16) Uani 1 1 d . A .
H15A H 0.7528 0.0502 0.3926 0.123 Uiso 1 1 calc R . .
H15B H 0.5784 0.0509 0.3939 0.123 Uiso 1 1 calc R . .
H15C H 0.6647 -0.0058 0.3997 0.123 Uiso 1 1 calc R . .
C16 C 0.7932(7) 0.0281(3) 0.4743(3) 0.0424(15) Uani 0.50 1 d P A 1
H16A H 0.7821 0.0474 0.5001 0.051 Uiso 0.50 1 calc PR A 1
H16B H 0.8871 0.0394 0.4623 0.051 Uiso 0.50 1 calc PR A 1
C16' C 0.7988(8) 0.0046(5) 0.4536(3) 0.059(2) Uani 0.50 1 d PU A 2
H16C H 0.7874 -0.0287 0.4369 0.070 Uiso 0.50 1 calc PR A 2
H16D H 0.8909 0.0230 0.4460 0.070 Uiso 0.50 1 calc PR A 2
C17 C 0.7921(8) -0.0354(4) 0.4811(3) 0.0441(17) Uani 0.50 1 d P A 1
H17A H 0.7872 -0.0550 0.4553 0.053 Uiso 0.50 1 calc PR A 1
H17B H 0.8814 -0.0471 0.4953 0.053 Uiso 0.50 1 calc PR A 1
C17' C 0.8019(9) -0.0104(5) 0.4958(4) 0.058(2) Uani 0.50 1 d PU A 2
H17C H 0.8006 0.0231 0.5125 0.069 Uiso 0.50 1 calc PR A 2
H17D H 0.8919 -0.0313 0.5018 0.069 Uiso 0.50 1 calc PR A 2
C18 C 0.6531(6) -0.1060(2) 0.49728(18) 0.0822(16) Uani 1 1 d . A .
H18A H 0.6304 -0.1123 0.4691 0.123 Uiso 1 1 calc R . .
H18B H 0.5756 -0.1218 0.5138 0.123 Uiso 1 1 calc R . .
H18C H 0.7462 -0.1236 0.5038 0.123 Uiso 1 1 calc R . .
C19 C 0.6640(4) -0.0390(2) 0.54841(14) 0.0613(11) Uani 1 1 d . A .
H19A H 0.7470 -0.0587 0.5600 0.092 Uiso 1 1 calc R . .
H19B H 0.5731 -0.0534 0.5597 0.092 Uiso 1 1 calc R . .
H19C H 0.6722 0.0002 0.5545 0.092 Uiso 1 1 calc R . .
Li1 Li 0.5000 0.0000 0.2926(3) 0.057(2) Uani 1 2 d S . .
Li2 Li 0.5000 0.0000 0.4767(2) 0.0326(13) Uani 1 2 d S . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C4 1.355(6) . ?
N1 C3 1.449(7) . ?
N1 Li1 1.942(4) . ?
N2 C15 1.437(7) . ?
N2 C14 1.460(6) . ?
N2 C16 1.488(8) . ?
N2 C16' 1.515(9) . ?
N2 Li2 2.126(5) . ?
N3 C17 1.451(8) . ?
N3 C18 1.466(7) . ?
N3 C19 1.475(6) . ?
N3 C17' 1.578(10) . ?
N3 Li2 2.107(4) . ?
C1 C2 1.268(13) . ?
C2 C3 1.499(11) . ?
C2 Li1 2.745(8) . ?
C3 Li1 2.714(7) . ?
C4 C5 1.387(5) . ?
C4 C13 1.456(5) . ?
C5 C6 1.438(8) . ?
C6 C7 1.356(9) . ?
C7 C8 1.383(8) . ?
C8 C13 1.424(6) . ?
C8 C9 1.458(8) . ?
C9 C10 1.347(9) . ?
C10 C11 1.339(9) . ?
C11 C12 1.414(6) . ?
C12 C13 1.424(5) . ?
C16 C17 1.562(10) . ?
C16 Li2 2.776(6) . ?
C16' C17' 1.462(13) . ?
Li1 N1 1.941(4) 2_655 ?
Li1 C3 2.714(7) 2_655 ?
Li1 C2 2.745(8) 2_655 ?
Li2 N3 2.107(4) 2_655 ?
Li2 N2 2.126(5) 2_655 ?
Li2 C16 2.776(6) 2_655 ?

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
C4 N1 C3 115.1(4) . . ?
C4 N1 Li1 133.9(4) . . ?
C3 N1 Li1 105.4(4) . . ?
C15 N2 C14 106.9(4) . . ?
C15 N2 C16 125.9(5) . . ?
C14 N2 C16 96.0(5) . . ?
C15 N2 C16' 93.7(5) . . ?
C14 N2 C16' 122.5(5) . . ?
C15 N2 Li2 111.2(3) . . ?
C14 N2 Li2 118.2(3) . . ?
C16 N2 Li2 98.8(4) . . ?
C16' N2 Li2 101.7(4) . . ?
C17 N3 C18 98.4(5) . . ?
C17 N3 C19 121.2(5) . . ?
C18 N3 C19 107.4(4) . . ?
C18 N3 C17' 124.8(6) . . ?
C19 N3 C17' 96.7(5) . . ?
C17 N3 Li2 103.2(4) . . ?
C18 N3 Li2 114.0(3) . . ?
C19 N3 Li2 112.2(3) . . ?
C17' N3 Li2 100.5(4) . . ?
C1 C2 C3 119.5(9) . . ?
C1 C2 Li1 108.5(5) . . ?
C3 C2 Li1 72.9(3) . . ?
N1 C3 C2 112.7(6) . . ?
C2 C3 Li1 75.2(4) . . ?
N1 C4 C5 126.7(4) . . ?
N1 C4 C13 118.4(3) . . ?
C5 C4 C13 114.8(4) . . ?
C4 C5 C6 121.8(4) . . ?
C7 C6 C5 122.6(4) . . ?
C6 C7 C8 118.0(5) . . ?
C7 C8 C13 121.3(5) . . ?
C7 C8 C9 121.7(5) . . ?
C13 C8 C9 117.0(5) . . ?
C10 C9 C8 123.3(5) . . ?
C11 C10 C9 119.2(5) . . ?
C10 C11 C12 122.3(5) . . ?
C11 C12 C13 120.2(5) . . ?
C8 C13 C12 117.8(4) . . ?
C8 C13 C4 121.4(3) . . ?
C12 C13 C4 120.7(3) . . ?
N2 C16 C17 108.9(6) . . ?
N2 C16 Li2 49.2(3) . . ?
C17 C16 Li2 75.3(4) . . ?
C17' C16' N2 107.7(8) . . ?
N3 C17 C16 106.0(6) . . ?
C16' C17' N3 108.1(8) . . ?
N1 Li1 N1 167.7(6) 2_655 . ?
N1 Li1 C3 152.34(16) 2_655 . ?
N1 Li1 C3 30.99(17) . . ?
N1 Li1 C3 30.99(17) 2_655 2_655 ?
N1 Li1 C3 152.34(16) . 2_655 ?
C3 Li1 C3 164.8(6) . 2_655 ?
N1 Li1 C2 127.8(3) 2_655 . ?
N1 Li1 C2 60.3(2) . . ?
C3 Li1 C2 31.9(2) . . ?
C3 Li1 C2 134.7(4) 2_655 . ?
N1 Li1 C2 60.3(2) 2_655 2_655 ?
N1 Li1 C2 127.8(3) . 2_655 ?
C3 Li1 C2 134.7(4) . 2_655 ?
C3 Li1 C2 31.9(2) 2_655 2_655 ?
C2 Li1 C2 113.2(5) . 2_655 ?
N3 Li2 N3 126.7(4) . 2_655 ?
N3 Li2 N2 87.15(10) . . ?
N3 Li2 N2 117.79(13) 2_655 . ?
N3 Li2 N2 117.79(13) . 2_655 ?
N3 Li2 N2 87.15(10) 2_655 2_655 ?
N2 Li2 N2 124.7(4) . 2_655 ?
N3 Li2 C16 124.7(2) . 2_655 ?
N3 Li2 C16 57.11(18) 2_655 2_655 ?
N2 Li2 C16 145.2(3) . 2_655 ?
N2 Li2 C16 32.00(19) 2_655 2_655 ?
N3 Li2 C16 57.11(18) . . ?
N3 Li2 C16 124.7(2) 2_655 . ?
N2 Li2 C16 32.00(19) . . ?
N2 Li2 C16 145.2(3) 2_655 . ?
C16 Li2 C16 176.7(5) 2_655 . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb229jg
_database_code_depnum_ccdc_archive 'CCDC 1472610'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H35 Li N4'
_chemical_formula_sum            'C22 H35 Li N4'
_chemical_formula_weight         362.48

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.0445(8)
_cell_length_b                   15.2792(11)
_cell_length_c                   15.5861(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2153.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3869
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.79

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7002
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10724
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4211
_reflns_number_gt                3718
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    XSeed
_computing_publication_material  CIF-TAB

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The compound was refined with a twin command and considered to be racemic

The naphthalene ring was moddeled as dissordered over two positions with 
70:30 occupancey. The carbon atom C4 and C4' was restrained and the C
to N atom bond length fixed (C4-N1 C4'-N1) with EDAP and SADI extra cards.

;

_vrf_STRVA01_vb229jg             
;
PROBLEM: Flack test results are meaningless.
RESPONSE: There is poor data:parameter ratio and the complex does not
contain a heavy atom - Li metal making the flack parameter meaningless
;

_chemical_absolute_configuration unk

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0441P)²+0.2107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(17)
_refine_ls_number_reflns         4211
_refine_ls_number_parameters     335
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
N1 N 0.59911(13) 0.81884(7) 0.14642(7) 0.0253(3) Uani 1 1 d D . .
N2 N 0.59429(12) 1.03551(7) 0.23257(7) 0.0256(3) Uani 1 1 d . . .
N3 N 0.41716(15) 1.01832(8) 0.07186(8) 0.0368(3) Uani 1 1 d . . .
N4 N 0.25238(13) 0.91433(8) 0.19480(9) 0.0359(3) Uani 1 1 d . . .
C1 C 0.60265(19) 0.79699(10) 0.05621(10) 0.0380(4) Uani 1 1 d . A .
H1A H 0.5047 0.8108 0.0313 0.046 Uiso 1 1 calc R . .
H1B H 0.6174 0.7330 0.0509 0.046 Uiso 1 1 calc R . .
C2 C 0.7190(2) 0.84217(11) 0.00310(11) 0.0443(4) Uani 1 1 d . . .
H2 H 0.7164 0.8328 -0.0571 0.053 Uiso 1 1 calc R A .
C3 C 0.8232(2) 0.89324(10) 0.03288(12) 0.0438(4) Uani 1 1 d . A .
H3A H 0.8298 0.9044 0.0927 0.053 Uiso 1 1 calc R . .
H3B H 0.8923 0.9192 -0.0054 0.053 Uiso 1 1 calc R . .
C4 C 0.702(2) 0.779(2) 0.1935(16) 0.028(2) Uani 0.717(6) 1 d PD A 1
C4' C 0.691(6) 0.779(6) 0.201(4) 0.028(2) Uani 0.28 1 d PD A 2
C5 C 0.8111(5) 0.7226(2) 0.1589(2) 0.0269(7) Uani 0.717(6) 1 d P A 1
H5 H 0.8092 0.7080 0.0997 0.032 Uiso 0.717(6) 1 calc PR A 1
C5' C 0.8272(13) 0.7310(7) 0.1935(6) 0.029(2) Uani 0.283(6) 1 d P A 2
H5' H 0.8510 0.7122 0.1371 0.035 Uiso 0.283(6) 1 calc PR A 2
C6 C 0.9205(4) 0.6886(2) 0.2119(3) 0.0380(9) Uani 0.717(6) 1 d P A 1
H6 H 0.9933 0.6512 0.1877 0.046 Uiso 0.717(6) 1 calc PR A 1
C6' C 0.9266(12) 0.7085(9) 0.2546(8) 0.035(3) Uani 0.283(6) 1 d P A 2
H6' H 1.0083 0.6729 0.2388 0.043 Uiso 0.283(6) 1 calc PR A 2
C7 C 0.9272(5) 0.7071(4) 0.2974(4) 0.0394(15) Uani 0.717(6) 1 d P A 1
H7 H 1.0076 0.6869 0.3313 0.047 Uiso 0.717(6) 1 calc PR A 1
C7' C 0.9140(13) 0.7352(6) 0.3388(8) 0.044(3) Uani 0.283(6) 1 d P A 2
H7' H 0.9907 0.7238 0.3789 0.053 Uiso 0.283(6) 1 calc PR A 2
C8 C 0.8128(6) 0.7565(3) 0.3345(3) 0.0366(10) Uani 0.717(6) 1 d P A 1
C8' C 0.7894(16) 0.7783(8) 0.3633(7) 0.035(3) Uani 0.283(6) 1 d P A 2
C9 C 0.8092(5) 0.7735(3) 0.4243(3) 0.0466(11) Uani 0.717(6) 1 d P A 1
H9 H 0.8898 0.7552 0.4589 0.056 Uiso 0.717(6) 1 calc PR A 1
C9' C 0.7580(16) 0.8039(12) 0.4473(11) 0.046(5) Uani 0.283(6) 1 d P A 2
H9' H 0.8306 0.7914 0.4896 0.056 Uiso 0.283(6) 1 calc PR A 2
C10 C 0.6936(6) 0.8152(5) 0.4614(4) 0.047(2) Uani 0.717(6) 1 d P A 1
H10 H 0.6941 0.8267 0.5213 0.057 Uiso 0.717(6) 1 calc PR A 1
C10' C 0.6331(18) 0.8453(7) 0.4742(8) 0.051(4) Uani 0.283(6) 1 d P A 2
H10' H 0.6222 0.8641 0.5320 0.061 Uiso 0.283(6) 1 calc PR A 2
C11 C 0.5733(7) 0.8413(4) 0.4110(5) 0.0455(13) Uani 0.717(6) 1 d P A 1
H11 H 0.4897 0.8671 0.4379 0.055 Uiso 0.717(6) 1 calc PR A 1
C11' C 0.5222(16) 0.8590(9) 0.4140(11) 0.034(3) Uani 0.283(6) 1 d P A 2
H11' H 0.4307 0.8852 0.4294 0.041 Uiso 0.283(6) 1 calc PR A 2
C12 C 0.5738(17) 0.8305(5) 0.3252(5) 0.039(3) Uani 0.717(6) 1 d P A 1
H12 H 0.4923 0.8502 0.2920 0.047 Uiso 0.717(6) 1 calc PR A 1
C12' C 0.552(4) 0.8314(11) 0.3265(12) 0.033(5) Uani 0.283(6) 1 d P A 2
H12' H 0.4740 0.8384 0.2864 0.039 Uiso 0.283(6) 1 calc PR A 2
C13 C 0.6995(9) 0.7887(5) 0.2835(6) 0.0280(16) Uani 0.717(6) 1 d P A 1
C13' C 0.6698(17) 0.7995(13) 0.2981(11) 0.013(2) Uani 0.283(6) 1 d P A 2
C14 C 0.74358(17) 1.01823(10) 0.26383(11) 0.0372(4) Uani 1 1 d . A .
H14A H 0.8009 0.9889 0.2189 0.056 Uiso 1 1 calc R . .
H14B H 0.7386 0.9805 0.3146 0.056 Uiso 1 1 calc R . .
H14C H 0.7915 1.0736 0.2790 0.056 Uiso 1 1 calc R . .
C15 C 0.50871(19) 1.07383(10) 0.30312(11) 0.0410(4) Uani 1 1 d . A .
H15A H 0.5050 1.0325 0.3511 0.061 Uiso 1 1 calc R . .
H15B H 0.4080 1.0864 0.2834 0.061 Uiso 1 1 calc R . .
H15C H 0.5560 1.1283 0.3220 0.061 Uiso 1 1 calc R . .
C16 C 0.60167(18) 1.09580(9) 0.15955(10) 0.0337(3) Uani 1 1 d . A .
H16A H 0.6785 1.0753 0.1190 0.040 Uiso 1 1 calc R . .
H16B H 0.6308 1.1546 0.1803 0.040 Uiso 1 1 calc R . .
C17 C 0.45644(19) 1.10239(9) 0.11325(11) 0.0406(4) Uani 1 1 d . A .
H17A H 0.3780 1.1189 0.1545 0.049 Uiso 1 1 calc R . .
H17B H 0.4627 1.1488 0.0691 0.049 Uiso 1 1 calc R . .
C18 C 0.4814(3) 1.01593(12) -0.01402(11) 0.0567(5) Uani 1 1 d . A .
H18A H 0.4568 0.9601 -0.0416 0.085 Uiso 1 1 calc R . .
H18B H 0.5891 1.0218 -0.0099 0.085 Uiso 1 1 calc R . .
H18C H 0.4415 1.0643 -0.0482 0.085 Uiso 1 1 calc R . .
C19 C 0.2558(2) 1.00878(12) 0.06592(14) 0.0553(5) Uani 1 1 d . A .
H19A H 0.2323 0.9610 0.0252 0.066 Uiso 1 1 calc R . .
H19B H 0.2131 1.0636 0.0428 0.066 Uiso 1 1 calc R . .
C20 C 0.18517(18) 0.98900(11) 0.15092(14) 0.0531(5) Uani 1 1 d . A .
H20A H 0.1931 1.0413 0.1882 0.064 Uiso 1 1 calc R . .
H20B H 0.0788 0.9769 0.1418 0.064 Uiso 1 1 calc R . .
C21 C 0.22187(17) 0.83279(10) 0.14925(12) 0.0411(4) Uani 1 1 d . A .
H21A H 0.1147 0.8245 0.1446 0.062 Uiso 1 1 calc R . .
H21B H 0.2652 0.7837 0.1809 0.062 Uiso 1 1 calc R . .
H21C H 0.2652 0.8355 0.0917 0.062 Uiso 1 1 calc R . .
C22 C 0.1895(2) 0.90899(13) 0.28096(13) 0.0579(5) Uani 1 1 d . A .
H22A H 0.2122 0.9628 0.3126 0.087 Uiso 1 1 calc R . .
H22B H 0.2320 0.8587 0.3112 0.087 Uiso 1 1 calc R . .
H22C H 0.0820 0.9019 0.2769 0.087 Uiso 1 1 calc R . .
Li1 Li 0.4880(2) 0.92781(14) 0.17020(15) 0.0246(5) Uani 1 1 d . A .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C4 1.333(4) . ?
N1 C4' 1.335(8) . ?
N1 C1 1.4454(18) . ?
N1 Li1 1.980(2) . ?
N2 C14 1.4595(18) . ?
N2 C16 1.4657(18) . ?
N2 C15 1.4666(19) . ?
N2 Li1 2.139(2) . ?
N3 C18 1.460(2) . ?
N3 C19 1.470(2) . ?
N3 C17 1.4807(19) . ?
N3 Li1 2.162(3) . ?
N4 C21 1.4602(19) . ?
N4 C22 1.461(2) . ?
N4 C20 1.463(2) . ?
N4 Li1 2.175(3) . ?
C1 C2 1.506(2) . ?
C2 C3 1.309(2) . ?
C4 C13 1.41(3) . ?
C4 C5 1.42(3) . ?
C4' C5' 1.44(6) . ?
C4' C13' 1.56(9) . ?
C5 C6 1.390(6) . ?
C5' C6' 1.354(14) . ?
C6 C7 1.364(5) . ?
C6' C7' 1.380(14) . ?
C7 C8 1.406(7) . ?
C7' C8' 1.359(17) . ?
C8 C13 1.387(11) . ?
C8 C9 1.424(5) . ?
C8' C9' 1.395(18) . ?
C8' C13' 1.52(2) . ?
C9 C10 1.354(7) . ?
C9' C10' 1.36(2) . ?
C10 C11 1.399(9) . ?
C10' C11' 1.39(3) . ?
C11 C12 1.348(11) . ?
C11' C12' 1.45(2) . ?
C12 C13 1.457(14) . ?
C12' C13' 1.25(4) . ?
C16 C17 1.502(2) . ?
C19 C20 1.501(3) . ?

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
C4 N1 C1 114.5(15) . . ?
C4' N1 C1 120(4) . . ?
C4 N1 Li1 129.4(17) . . ?
C4' N1 Li1 125(4) . . ?
C1 N1 Li1 112.81(11) . . ?
C14 N2 C16 109.31(11) . . ?
C14 N2 C15 108.07(12) . . ?
C16 N2 C15 110.81(11) . . ?
C14 N2 Li1 115.35(10) . . ?
C16 N2 Li1 98.68(10) . . ?
C15 N2 Li1 114.25(10) . . ?
C18 N3 C19 109.58(14) . . ?
C18 N3 C17 109.01(13) . . ?
C19 N3 C17 110.60(14) . . ?
C18 N3 Li1 121.07(13) . . ?
C19 N3 Li1 106.00(12) . . ?
C17 N3 Li1 100.08(10) . . ?
C21 N4 C22 109.01(13) . . ?
C21 N4 C20 111.09(14) . . ?
C22 N4 C20 108.16(14) . . ?
C21 N4 Li1 100.39(11) . . ?
C22 N4 Li1 123.29(13) . . ?
C20 N4 Li1 104.53(11) . . ?
N1 C1 C2 116.38(13) . . ?
C3 C2 C1 125.55(15) . . ?
N1 C4 C13 119(2) . . ?
N1 C4 C5 124(2) . . ?
C13 C4 C5 117.0(4) . . ?
N1 C4' C5' 136(6) . . ?
N1 C4' C13' 117(5) . . ?
C5' C4' C13' 106.6(19) . . ?
C6 C5 C4 119.8(8) . . ?
C6' C5' C4' 130(3) . . ?
C7 C6 C5 122.3(4) . . ?
C5' C6' C7' 122.6(10) . . ?
C6 C7 C8 118.7(5) . . ?
C8' C7' C6' 118.6(10) . . ?
C13 C8 C7 119.9(5) . . ?
C13 C8 C9 118.8(5) . . ?
C7 C8 C9 121.2(5) . . ?
C7' C8' C9' 124.7(12) . . ?
C7' C8' C13' 120.4(10) . . ?
C9' C8' C13' 114.9(12) . . ?
C10 C9 C8 121.6(5) . . ?
C10' C9' C8' 126.1(17) . . ?
C9 C10 C11 119.6(6) . . ?
C9' C10' C11' 117.4(15) . . ?
C12 C11 C10 121.3(8) . . ?
C10' C11' C12' 117.1(16) . . ?
C11 C12 C13 119.9(9) . . ?
C13' C12' C11' 127(2) . . ?
C8 C13 C4 121.4(9) . . ?
C8 C13 C12 118.4(7) . . ?
C4 C13 C12 120.2(9) . . ?
C12' C13' C8' 116.9(16) . . ?
C12' C13' C4' 121.8(19) . . ?
C8' C13' C4' 121.3(16) . . ?
N2 C16 C17 112.05(12) . . ?
N3 C17 C16 111.16(12) . . ?
N3 C19 C20 112.75(14) . . ?
N4 C20 C19 113.14(14) . . ?
N1 Li1 N2 120.27(12) . . ?
N1 Li1 N3 123.77(12) . . ?
N2 Li1 N3 87.90(9) . . ?
N1 Li1 N4 116.78(11) . . ?
N2 Li1 N4 115.65(11) . . ?
N3 Li1 N4 83.97(10) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.029
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
