# Electronic Supplementary Material (ESI) for ChemComm.
# 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_vb223ms
_database_code_depnum_ccdc_archive 'CCDC 1452498'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H30 Li N3'
_chemical_formula_sum            'C21 H30 Li N3'
_chemical_formula_weight         331.42

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           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   10.1048(8)
_cell_length_b                   12.9834(8)
_cell_length_c                   15.3410(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.567(4)
_cell_angle_gamma                90.00
_cell_volume                     1964.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    14264
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.93

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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            14246
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         28.03
_reflns_number_total             8649
_reflns_number_gt                7646
_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    XSEED
_computing_publication_material  CIFTAB

_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. 
;

_vrf_STRVA01_vb223ms             
;
PROBLEM: Flack parameter is too small
RESPONSE: The complex does not contain any heavy atoms so the flack
parameter is unreliable. The compound composition is confirmed by
othe analytical methods NMR, Microanalysis etc.
;

_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)+(0.0619P)²+0.1773P] 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   -1.1(14)
_refine_ls_number_reflns         8649
_refine_ls_number_parameters     459
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration .

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 -0.28059(14) 0.48378(11) 0.44473(9) 0.0219(3) Uani 1 1 d . . .
N2 N -0.00610(14) 0.32602(11) 0.37257(9) 0.0204(3) Uani 1 1 d . . .
N3 N 0.16439(15) 0.49677(10) 0.44822(9) 0.0223(3) Uani 1 1 d . . .
N4 N -0.34525(14) 0.65207(10) -0.17138(9) 0.0208(3) Uani 1 1 d . . .
N5 N -0.23512(17) 0.45228(13) 0.01043(10) 0.0315(4) Uani 1 1 d . . .
N6 N -0.17429(15) 0.33428(12) -0.13841(10) 0.0274(3) Uani 1 1 d . . .
C1 C -0.18825(17) 0.52775(13) 0.52032(11) 0.0223(3) Uani 1 1 d . . .
H1 H -0.1864 0.6005 0.5274 0.027 Uiso 1 1 calc R . .
C2 C -0.10198(17) 0.46846(13) 0.58310(10) 0.0221(3) Uani 1 1 d . . .
H2 H -0.0551 0.5056 0.6339 0.027 Uiso 1 1 calc R . .
C3 C -0.07254(18) 0.36510(14) 0.58453(11) 0.0251(4) Uani 1 1 d . . .
H3A H -0.1150 0.3223 0.5363 0.030 Uiso 1 1 calc R . .
H3B H -0.0097 0.3365 0.6337 0.030 Uiso 1 1 calc R . .
C4 C -0.31187(17) 0.54315(13) 0.36628(11) 0.0217(3) Uani 1 1 d . . .
C5 C -0.21945(18) 0.61635(14) 0.34946(12) 0.0278(4) Uani 1 1 d . . .
H5 H -0.1350 0.6243 0.3906 0.033 Uiso 1 1 calc R . .
C6 C -0.2487(2) 0.67751(15) 0.27394(13) 0.0334(4) Uani 1 1 d . . .
H6 H -0.1842 0.7270 0.2641 0.040 Uiso 1 1 calc R . .
C7 C -0.3707(2) 0.66767(16) 0.21245(13) 0.0350(4) Uani 1 1 d . . .
H7 H -0.3901 0.7093 0.1603 0.042 Uiso 1 1 calc R . .
C8 C -0.4627(2) 0.59652(15) 0.22857(12) 0.0321(4) Uani 1 1 d . . .
H8 H -0.5468 0.5892 0.1869 0.039 Uiso 1 1 calc R . .
C9 C -0.43610(18) 0.53515(14) 0.30401(12) 0.0267(4) Uani 1 1 d . . .
H9 H -0.5023 0.4872 0.3139 0.032 Uiso 1 1 calc R . .
C10 C -0.36469(16) 0.39990(13) 0.45828(11) 0.0204(3) Uani 1 1 d . . .
C11 C -0.40330(16) 0.32460(13) 0.39247(11) 0.0231(3) Uani 1 1 d . . .
H11 H -0.3777 0.3316 0.3367 0.028 Uiso 1 1 calc R . .
C12 C -0.47810(18) 0.24036(14) 0.40757(12) 0.0266(4) Uani 1 1 d . . .
H12 H -0.5041 0.1900 0.3621 0.032 Uiso 1 1 calc R . .
C13 C -0.51556(18) 0.22857(14) 0.48831(13) 0.0288(4) Uani 1 1 d . . .
H13 H -0.5674 0.1705 0.4985 0.035 Uiso 1 1 calc R . .
C14 C -0.47690(18) 0.30205(14) 0.55439(12) 0.0277(4) Uani 1 1 d . . .
H14 H -0.5020 0.2942 0.6102 0.033 Uiso 1 1 calc R . .
C15 C -0.40159(17) 0.38720(14) 0.53953(11) 0.0245(4) Uani 1 1 d . . .
H15 H -0.3752 0.4371 0.5853 0.029 Uiso 1 1 calc R . .
C16 C -0.06471(19) 0.22537(13) 0.38377(12) 0.0251(4) Uani 1 1 d . . .
H16A H -0.1635 0.2317 0.3743 0.038 Uiso 1 1 calc R . .
H16B H -0.0279 0.1999 0.4443 0.038 Uiso 1 1 calc R . .
H16C H -0.0422 0.1769 0.3402 0.038 Uiso 1 1 calc R . .
C17 C -0.0550(2) 0.35977(15) 0.27989(11) 0.0293(4) Uani 1 1 d . . .
H17A H -0.0201 0.3134 0.2398 0.044 Uiso 1 1 calc R . .
H17B H -0.0233 0.4300 0.2730 0.044 Uiso 1 1 calc R . .
H17C H -0.1544 0.3585 0.2650 0.044 Uiso 1 1 calc R . .
C18 C 0.14290(17) 0.31696(13) 0.39609(11) 0.0211(3) Uani 1 1 d . . .
H18A H 0.1725 0.2680 0.3546 0.025 Uiso 1 1 calc R . .
H18B H 0.1710 0.2887 0.4573 0.025 Uiso 1 1 calc R . .
C19 C 0.21188(18) 0.41918(13) 0.39162(11) 0.0229(3) Uani 1 1 d . . .
H19A H 0.3112 0.4104 0.4117 0.027 Uiso 1 1 calc R . .
H19B H 0.1928 0.4436 0.3290 0.027 Uiso 1 1 calc R . .
C20 C 0.2455(2) 0.49009(15) 0.54000(12) 0.0307(4) Uani 1 1 d . . .
H20A H 0.2376 0.4207 0.5635 0.046 Uiso 1 1 calc R . .
H20B H 0.2123 0.5406 0.5776 0.046 Uiso 1 1 calc R . .
H20C H 0.3408 0.5045 0.5401 0.046 Uiso 1 1 calc R . .
C21 C 0.1786(2) 0.60008(15) 0.41282(14) 0.0337(4) Uani 1 1 d . . .
H21A H 0.1525 0.6517 0.4526 0.051 Uiso 1 1 calc R . .
H21B H 0.1197 0.6064 0.3532 0.051 Uiso 1 1 calc R . .
H21C H 0.2731 0.6113 0.4090 0.051 Uiso 1 1 calc R . .
C22 C -0.25265(17) 0.61437(13) -0.22306(10) 0.0210(3) Uani 1 1 d . . .
H22 H -0.2867 0.5929 -0.2830 0.025 Uiso 1 1 calc R . .
C23 C -0.11555(17) 0.60882(13) -0.18727(11) 0.0219(3) Uani 1 1 d . . .
H23 H -0.0612 0.5933 -0.2289 0.026 Uiso 1 1 calc R . .
C24 C -0.04426(17) 0.62235(14) -0.09990(11) 0.0253(4) Uani 1 1 d . . .
H24A H -0.0914 0.6381 -0.0543 0.030 Uiso 1 1 calc R . .
H24B H 0.0517 0.6159 -0.0857 0.030 Uiso 1 1 calc R . .
C25 C -0.31964(16) 0.75041(13) -0.13007(11) 0.0206(3) Uani 1 1 d . . .
C26 C -0.26903(19) 0.82994(14) -0.17329(12) 0.0283(4) Uani 1 1 d . . .
H26 H -0.2553 0.8200 -0.2320 0.034 Uiso 1 1 calc R . .
C27 C -0.2384(2) 0.92390(15) -0.13120(14) 0.0357(4) Uani 1 1 d . . .
H27 H -0.2041 0.9781 -0.1615 0.043 Uiso 1 1 calc R . .
C42 C -0.33688(18) 0.76675(14) -0.04365(11) 0.0261(4) Uani 1 1 d . . .
H42 H -0.3702 0.7126 -0.0127 0.031 Uiso 1 1 calc R . .
C28 C -0.2571(2) 0.93994(15) -0.04591(14) 0.0351(5) Uani 1 1 d . . .
H28 H -0.2364 1.0048 -0.0176 0.042 Uiso 1 1 calc R . .
C29 C -0.30618(19) 0.86079(16) -0.00231(12) 0.0312(4) Uani 1 1 d . . .
H29 H -0.3190 0.8710 0.0566 0.037 Uiso 1 1 calc R . .
C30 C -0.47489(16) 0.60885(13) -0.18516(9) 0.0198(3) Uani 1 1 d . . .
C31 C -0.58545(18) 0.66142(14) -0.16572(11) 0.0250(4) Uani 1 1 d . . .
H31 H -0.5740 0.7297 -0.1431 0.030 Uiso 1 1 calc R . .
C32 C -0.71139(18) 0.61520(16) -0.17903(11) 0.0301(4) Uani 1 1 d . . .
H32 H -0.7851 0.6518 -0.1646 0.036 Uiso 1 1 calc R . .
C33 C -0.73187(19) 0.51628(15) -0.21314(12) 0.0307(4) Uani 1 1 d . . .
H33 H -0.8185 0.4846 -0.2215 0.037 Uiso 1 1 calc R . .
C34 C -0.62461(19) 0.46492(14) -0.23461(11) 0.0287(4) Uani 1 1 d . . .
H34 H -0.6377 0.3973 -0.2586 0.034 Uiso 1 1 calc R . .
C35 C -0.49758(18) 0.50993(13) -0.22191(11) 0.0241(4) Uani 1 1 d . . .
H35 H -0.4252 0.4734 -0.2383 0.029 Uiso 1 1 calc R . .
C36 C -0.3792(2) 0.45280(19) 0.01281(14) 0.0402(5) Uani 1 1 d . . .
H36A H -0.4290 0.4072 -0.0339 0.060 Uiso 1 1 calc R . .
H36B H -0.4149 0.5230 0.0027 0.060 Uiso 1 1 calc R . .
H36C H -0.3903 0.4285 0.0713 0.060 Uiso 1 1 calc R . .
C37 C -0.1636(2) 0.52045(17) 0.08332(13) 0.0391(5) Uani 1 1 d . . .
H37A H -0.1782 0.4952 0.1407 0.059 Uiso 1 1 calc R . .
H37B H -0.1991 0.5907 0.0731 0.059 Uiso 1 1 calc R . .
H37C H -0.0663 0.5204 0.0842 0.059 Uiso 1 1 calc R . .
C38 C -0.1749(2) 0.34936(16) 0.02304(13) 0.0402(5) Uani 1 1 d . . .
H38A H -0.2059 0.3141 0.0723 0.048 Uiso 1 1 calc R . .
H38B H -0.0749 0.3556 0.0402 0.048 Uiso 1 1 calc R . .
C39 C -0.2139(2) 0.28503(16) -0.06161(13) 0.0381(5) Uani 1 1 d . . .
H39A H -0.1695 0.2168 -0.0511 0.046 Uiso 1 1 calc R . .
H39B H -0.3132 0.2739 -0.0757 0.046 Uiso 1 1 calc R . .
C40 C -0.2498(2) 0.28892(15) -0.22131(12) 0.0335(4) Uani 1 1 d . . .
H40A H -0.2257 0.3241 -0.2722 0.050 Uiso 1 1 calc R . .
H40B H -0.3473 0.2965 -0.2246 0.050 Uiso 1 1 calc R . .
H40C H -0.2273 0.2156 -0.2229 0.050 Uiso 1 1 calc R . .
C41 C -0.0295(2) 0.3218(2) -0.13462(18) 0.0473(5) Uani 1 1 d . . .
H41A H -0.0084 0.2485 -0.1382 0.071 Uiso 1 1 calc R . .
H41B H 0.0224 0.3503 -0.0783 0.071 Uiso 1 1 calc R . .
H41C H -0.0054 0.3584 -0.1848 0.071 Uiso 1 1 calc R . .
Li1 Li -0.0249(3) 0.4402(2) 0.46345(19) 0.0263(6) Uani 1 1 d . . .
Li2 Li -0.1959(3) 0.4925(2) -0.11299(19) 0.0270(6) 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
N1 C4 1.406(2) . ?
N1 C10 1.424(2) . ?
N1 C1 1.439(2) . ?
N1 Li1 2.599(3) . ?
N2 C16 1.460(2) . ?
N2 C17 1.467(2) . ?
N2 C18 1.475(2) . ?
N2 Li1 2.072(3) . ?
N3 C21 1.466(2) . ?
N3 C20 1.470(2) . ?
N3 C19 1.477(2) . ?
N3 Li1 2.109(3) . ?
N4 C30 1.398(2) . ?
N4 C25 1.424(2) . ?
N4 C22 1.438(2) . ?
N4 Li2 2.605(3) . ?
N5 C36 1.465(3) . ?
N5 C38 1.464(3) . ?
N5 C37 1.485(3) . ?
N5 Li2 2.083(3) . ?
N6 C40 1.458(2) . ?
N6 C41 1.460(3) . ?
N6 C39 1.470(2) . ?
N6 Li2 2.111(3) . ?
C1 C2 1.384(2) . ?
C1 Li1 2.325(3) . ?
C2 C3 1.374(2) . ?
C2 Li1 2.175(3) . ?
C3 Li1 2.241(3) . ?
C4 C5 1.395(3) . ?
C4 C9 1.406(2) . ?
C5 C6 1.382(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.382(3) . ?
C10 C15 1.386(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.377(2) . ?
C12 C13 1.380(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.389(3) . ?
C18 C19 1.508(2) . ?
C18 Li1 2.696(3) . ?
C22 C23 1.377(2) . ?
C22 Li2 2.294(3) . ?
C23 C24 1.388(2) . ?
C23 Li2 2.155(3) . ?
C24 Li2 2.258(4) . ?
C25 C26 1.384(3) . ?
C25 C42 1.391(2) . ?
C26 C27 1.383(3) . ?
C27 C28 1.378(3) . ?
C42 C29 1.380(3) . ?
C28 C29 1.376(3) . ?
C30 C31 1.396(2) . ?
C30 C35 1.401(2) . ?
C31 C32 1.381(3) . ?
C32 C33 1.385(3) . ?
C33 C34 1.372(3) . ?
C34 C35 1.385(3) . ?
C38 C39 1.522(3) . ?
C38 Li2 2.768(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 C10 120.93(13) . . ?
C4 N1 C1 117.26(14) . . ?
C10 N1 C1 119.25(13) . . ?
C4 N1 Li1 104.29(12) . . ?
C10 N1 Li1 115.33(12) . . ?
C1 N1 Li1 62.78(11) . . ?
C16 N2 C17 108.76(13) . . ?
C16 N2 C18 108.57(13) . . ?
C17 N2 C18 111.83(14) . . ?
C16 N2 Li1 117.53(14) . . ?
C17 N2 Li1 112.17(14) . . ?
C18 N2 Li1 97.51(12) . . ?
C21 N3 C20 109.26(15) . . ?
C21 N3 C19 109.63(14) . . ?
C20 N3 C19 109.76(14) . . ?
C21 N3 Li1 121.60(15) . . ?
C20 N3 Li1 101.76(13) . . ?
C19 N3 Li1 104.25(13) . . ?
C30 N4 C25 120.05(14) . . ?
C30 N4 C22 118.74(13) . . ?
C25 N4 C22 118.27(14) . . ?
C30 N4 Li2 100.74(12) . . ?
C25 N4 Li2 121.65(11) . . ?
C22 N4 Li2 61.38(10) . . ?
C36 N5 C38 112.83(17) . . ?
C36 N5 C37 107.60(17) . . ?
C38 N5 C37 108.93(15) . . ?
C36 N5 Li2 114.09(14) . . ?
C38 N5 Li2 101.13(15) . . ?
C37 N5 Li2 112.17(15) . . ?
C40 N6 C41 108.66(17) . . ?
C40 N6 C39 109.96(15) . . ?
C41 N6 C39 111.39(17) . . ?
C40 N6 Li2 119.91(14) . . ?
C41 N6 Li2 104.08(15) . . ?
C39 N6 Li2 102.59(15) . . ?
C2 C1 N1 122.69(15) . . ?
C2 C1 Li1 66.30(12) . . ?
N1 C1 Li1 83.82(12) . . ?
C3 C2 C1 131.00(16) . . ?
C3 C2 Li1 74.49(13) . . ?
C1 C2 Li1 78.08(13) . . ?
C2 C3 Li1 69.30(12) . . ?
C5 C4 N1 119.79(15) . . ?
C5 C4 C9 117.33(16) . . ?
N1 C4 C9 122.84(16) . . ?
C6 C5 C4 121.11(16) . . ?
C5 C6 C7 120.93(18) . . ?
C8 C7 C6 118.50(17) . . ?
C7 C8 C9 121.55(17) . . ?
C8 C9 C4 120.57(17) . . ?
C15 C10 C11 118.58(16) . . ?
C15 C10 N1 120.53(14) . . ?
C11 C10 N1 120.72(15) . . ?
C12 C11 C10 120.71(16) . . ?
C11 C12 C13 120.44(16) . . ?
C12 C13 C14 119.46(17) . . ?
C13 C14 C15 120.37(18) . . ?
C10 C15 C14 120.43(16) . . ?
N2 C18 C19 112.10(13) . . ?
N2 C18 Li1 49.65(9) . . ?
C19 C18 Li1 80.24(11) . . ?
N3 C19 C18 111.18(14) . . ?
C23 C22 N4 121.15(14) . . ?
C23 C22 Li2 66.53(12) . . ?
N4 C22 Li2 85.25(12) . . ?
C22 C23 C24 130.12(16) . . ?
C22 C23 Li2 77.60(13) . . ?
C24 C23 Li2 75.77(13) . . ?
C23 C24 Li2 67.66(12) . . ?
C26 C25 C42 118.62(15) . . ?
C26 C25 N4 120.42(15) . . ?
C42 C25 N4 120.85(15) . . ?
C27 C26 C25 120.19(17) . . ?
C28 C27 C26 120.90(19) . . ?
C29 C42 C25 120.73(17) . . ?
C29 C28 C27 119.14(17) . . ?
C28 C29 C42 120.41(17) . . ?
C31 C30 N4 122.59(15) . . ?
C31 C30 C35 117.75(16) . . ?
N4 C30 C35 119.64(15) . . ?
C32 C31 C30 120.70(17) . . ?
C31 C32 C33 121.04(18) . . ?
C34 C33 C32 118.70(17) . . ?
C33 C34 C35 121.16(18) . . ?
C34 C35 C30 120.59(17) . . ?
N5 C38 C39 111.43(16) . . ?
N5 C38 Li2 47.61(11) . . ?
C39 C38 Li2 76.23(12) . . ?
N6 C39 C38 112.34(16) . . ?
N2 Li1 N3 87.50(13) . . ?
N2 Li1 C2 142.23(17) . . ?
N3 Li1 C2 122.32(14) . . ?
N2 Li1 C3 108.31(14) . . ?
N3 Li1 C3 127.37(15) . . ?
C2 Li1 C3 36.20(8) . . ?
N2 Li1 C1 141.17(16) . . ?
N3 Li1 C1 127.33(15) . . ?
C2 Li1 C1 35.62(8) . . ?
C3 Li1 C1 66.65(10) . . ?
N2 Li1 N1 108.42(13) . . ?
N3 Li1 N1 144.66(15) . . ?
C2 Li1 N1 61.75(9) . . ?
C3 Li1 N1 78.39(11) . . ?
C1 Li1 N1 33.39(6) . . ?
N2 Li1 C18 32.84(7) . . ?
N3 Li1 C18 60.19(9) . . ?
C2 Li1 C18 142.57(15) . . ?
C3 Li1 C18 109.02(13) . . ?
C1 Li1 C18 172.46(15) . . ?
N1 Li1 C18 141.26(13) . . ?
N5 Li2 N6 88.39(13) . . ?
N5 Li2 C23 145.52(17) . . ?
N6 Li2 C23 121.22(16) . . ?
N5 Li2 C24 111.46(14) . . ?
N6 Li2 C24 130.35(16) . . ?
C23 Li2 C24 36.57(8) . . ?
N5 Li2 C22 140.83(17) . . ?
N6 Li2 C22 123.68(15) . . ?
C23 Li2 C22 35.88(7) . . ?
C24 Li2 C22 66.82(10) . . ?
N5 Li2 N4 107.54(14) . . ?
N6 Li2 N4 141.82(14) . . ?
C23 Li2 N4 61.14(9) . . ?
C24 Li2 N4 76.57(10) . . ?
C22 Li2 N4 33.37(6) . . ?
N5 Li2 C38 31.26(8) . . ?
N6 Li2 C38 59.46(9) . . ?
C23 Li2 C38 153.31(15) . . ?
C24 Li2 C38 119.67(13) . . ?
C22 Li2 C38 169.75(16) . . ?
N4 Li2 C38 137.49(14) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.045
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive, Pyrophoric'
####################################################################### 
# 
# 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_vb170
_database_code_depnum_ccdc_archive 'CCDC 1452499'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H48 Li2 O2 P2'
_chemical_formula_sum            'C38 H48 Li2 O2 P2'
_chemical_formula_weight         612.58

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

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'

_cell_length_a                   10.592(2)
_cell_length_b                   18.626(4)
_cell_length_c                   9.1190(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.24(3)
_cell_angle_gamma                90.00
_cell_volume                     1791.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13140
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.93

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 210r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14517
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.96
_reflns_number_total             4215
_reflns_number_gt                4111
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_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. 
;

_vrf_PLAT230_vb170               
;
PROBLEM: Hirshfeld Test Diff for    P1     --  C1      ..        6.4 s.u.  
RESPONSE: The P-C bond ESD is small however we are confident in the atom
assignment
;

_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)+(0.0500P)²+1.0616P] 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   0.01(7)
_refine_ls_number_reflns         4215
_refine_ls_number_parameters     201
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
P1 P 0.71847(4) 0.091182(18) 0.33567(4) 0.01598(9) Uani 1 1 d . . .
O1 O 0.59877(12) 0.14635(6) 0.66961(14) 0.0263(3) Uani 1 1 d . . .
C1 C 0.65507(14) 0.05914(8) 0.16267(17) 0.0196(3) Uani 1 1 d . . .
H1 H 0.7081 0.0517 0.0855 0.023 Uiso 1 1 calc R . .
C2 C 0.52338(14) 0.04469(8) 0.14094(17) 0.0192(3) Uani 1 1 d . . .
H2 H 0.4796 0.0421 0.2272 0.023 Uiso 1 1 calc R . .
C3 C 0.45198(17) 0.03402(9) 0.0099(2) 0.0267(3) Uani 1 1 d . . .
H3A H 0.4907 0.0360 -0.0800 0.032 Uiso 1 1 calc R . .
H3B H 0.3637 0.0247 0.0088 0.032 Uiso 1 1 calc R . .
C4 C 0.89042(14) 0.08018(8) 0.33398(16) 0.0180(3) Uani 1 1 d . . .
C5 C 0.95926(15) 0.03959(9) 0.44142(18) 0.0224(3) Uani 1 1 d . . .
H5 H 0.9169 0.0171 0.5166 0.027 Uiso 1 1 calc R . .
C6 C 1.09030(16) 0.03158(10) 0.4397(2) 0.0275(3) Uani 1 1 d . . .
H6 H 1.1365 0.0038 0.5137 0.033 Uiso 1 1 calc R . .
C7 C 1.15314(15) 0.06402(10) 0.3307(2) 0.0262(3) Uani 1 1 d . . .
H7 H 1.2421 0.0582 0.3295 0.031 Uiso 1 1 calc R . .
C8 C 1.08562(16) 0.10509(10) 0.2232(2) 0.0244(3) Uani 1 1 d . . .
H8 H 1.1285 0.1277 0.1486 0.029 Uiso 1 1 calc R . .
C9 C 0.95582(15) 0.11300(9) 0.22496(18) 0.0215(3) Uani 1 1 d . . .
H9 H 0.9103 0.1411 0.1511 0.026 Uiso 1 1 calc R . .
C10 C 0.71215(17) 0.19035(7) 0.32440(19) 0.0197(3) Uani 1 1 d . . .
C11 C 0.62919(16) 0.22472(10) 0.2186(2) 0.0249(4) Uani 1 1 d . . .
H11 H 0.5781 0.1970 0.1487 0.030 Uiso 1 1 calc R . .
C12 C 0.62115(19) 0.29936(10) 0.2152(2) 0.0327(4) Uani 1 1 d . . .
H12 H 0.5649 0.3224 0.1428 0.039 Uiso 1 1 calc R . .
C13 C 0.69485(19) 0.34013(9) 0.3171(2) 0.0339(5) Uani 1 1 d . . .
H13 H 0.6889 0.3910 0.3145 0.041 Uiso 1 1 calc R . .
C14 C 0.77677(19) 0.30724(10) 0.4223(2) 0.0295(4) Uani 1 1 d . . .
H14 H 0.8275 0.3353 0.4918 0.035 Uiso 1 1 calc R . .
C15 C 0.78500(17) 0.23243(9) 0.42645(19) 0.0235(3) Uani 1 1 d . . .
H15 H 0.8410 0.2099 0.4998 0.028 Uiso 1 1 calc R . .
C16 C 0.6913(2) 0.17553(10) 0.7779(2) 0.0329(4) Uani 1 1 d . . .
H16A H 0.6533 0.1820 0.8723 0.039 Uiso 1 1 calc R . .
H16B H 0.7199 0.2230 0.7451 0.039 Uiso 1 1 calc R . .
C17 C 0.8022(2) 0.12522(11) 0.7993(2) 0.0345(4) Uani 1 1 d . . .
H17A H 0.7733 0.0783 0.8315 0.052 Uiso 1 1 calc R . .
H17B H 0.8652 0.1448 0.8742 0.052 Uiso 1 1 calc R . .
H17C H 0.8406 0.1198 0.7061 0.052 Uiso 1 1 calc R . .
C18 C 0.50283(18) 0.19916(10) 0.6233(2) 0.0340(4) Uani 1 1 d . . .
H18A H 0.5426 0.2406 0.5775 0.041 Uiso 1 1 calc R . .
H18B H 0.4620 0.2167 0.7099 0.041 Uiso 1 1 calc R . .
C19 C 0.40553(18) 0.16614(11) 0.5152(3) 0.0378(4) Uani 1 1 d . . .
H19A H 0.4458 0.1505 0.4281 0.057 Uiso 1 1 calc R . .
H19B H 0.3396 0.2016 0.4861 0.057 Uiso 1 1 calc R . .
H19C H 0.3673 0.1247 0.5604 0.057 Uiso 1 1 calc R . .
Li2 Li 0.6187(3) 0.05343(14) 0.5731(3) 0.0223(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
P1 C1 1.7614(17) . ?
P1 C4 1.8343(16) . ?
P1 C10 1.8508(15) . ?
P1 Li2 2.592(3) . ?
O1 C16 1.434(2) . ?
O1 C18 1.449(2) . ?
O1 Li2 1.962(3) . ?
C1 C2 1.417(2) . ?
C1 Li2 2.270(3) 2_554 ?
C2 C3 1.369(2) . ?
C2 Li2 2.203(3) 2_554 ?
C3 Li2 2.432(3) 2_554 ?
C4 C5 1.390(2) . ?
C4 C9 1.403(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.384(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.384(2) . ?
C10 C15 1.394(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.393(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.396(2) . ?
C16 C17 1.501(3) . ?
C18 C19 1.492(3) . ?
Li2 C2 2.203(3) 2 ?
Li2 C1 2.270(3) 2 ?
Li2 C3 2.432(3) 2 ?

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
C1 P1 C4 104.61(8) . . ?
C1 P1 C10 106.24(8) . . ?
C4 P1 C10 98.16(7) . . ?
C1 P1 Li2 120.34(8) . . ?
C4 P1 Li2 117.24(8) . . ?
C10 P1 Li2 107.56(8) . . ?
C16 O1 C18 111.14(14) . . ?
C16 O1 Li2 123.29(14) . . ?
C18 O1 Li2 124.71(14) . . ?
C2 C1 P1 118.66(12) . . ?
C2 C1 Li2 68.99(11) . 2_554 ?
P1 C1 Li2 132.34(11) . 2_554 ?
C3 C2 C1 127.45(16) . . ?
C3 C2 Li2 82.26(12) . 2_554 ?
C1 C2 Li2 74.12(11) . 2_554 ?
C2 C3 Li2 63.84(11) . 2_554 ?
C5 C4 C9 118.38(14) . . ?
C5 C4 P1 120.80(12) . . ?
C9 C4 P1 120.81(12) . . ?
C4 C5 C6 120.51(15) . . ?
C7 C6 C5 120.31(16) . . ?
C6 C7 C8 119.78(15) . . ?
C9 C8 C7 119.89(15) . . ?
C8 C9 C4 121.14(15) . . ?
C15 C10 C11 118.51(14) . . ?
C15 C10 P1 120.59(13) . . ?
C11 C10 P1 120.80(13) . . ?
C12 C11 C10 120.32(17) . . ?
C13 C12 C11 120.21(18) . . ?
C14 C13 C12 120.28(15) . . ?
C13 C14 C15 119.78(17) . . ?
C10 C15 C14 120.89(17) . . ?
O1 C16 C17 109.30(15) . . ?
O1 C18 C19 109.66(15) . . ?
O1 Li2 C2 122.36(15) . 2 ?
O1 Li2 C1 132.47(15) . 2 ?
C2 Li2 C1 36.89(7) 2 2 ?
O1 Li2 C3 126.28(15) . 2 ?
C2 Li2 C3 33.90(7) 2 2 ?
C1 Li2 C3 64.06(9) 2 2 ?
O1 Li2 P1 101.78(11) . . ?
C2 Li2 P1 133.76(13) 2 . ?
C1 Li2 P1 118.83(12) 2 . ?
C3 Li2 P1 109.04(12) 2 . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_vb225
_database_code_depnum_ccdc_archive 'CCDC 1452869'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H37 Li N4'
_chemical_formula_sum            'C24 H37 Li N4'
_chemical_formula_weight         388.52

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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'

_cell_length_a                   10.1275(4)
_cell_length_b                   8.6095(3)
_cell_length_c                   27.5008(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.558(3)
_cell_angle_gamma                90.00
_cell_volume                     2396.98(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    13465
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.96

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  0.7453
_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            13075
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         26.08
_reflns_number_total             4754
_reflns_number_gt                3058
_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 PMDETA C16-C24 and N2-N4 was modelled as dissordered over
two positions with half occupancy.Atoms C16, C16', C26, C26', N4 and N4'
were restrained with SIMU commands
;

_vrf_PLAT213_vb225               
;
PROBLEM: Atom C23'            has ADP max/min Ratio .....        3.2 prolat
RESPONSE: This atom is part of the modelled dissorder of the PMDETA
molecule see cif for further details
;

_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)+(0.0439P)²+0.4251P] 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         4754
_refine_ls_number_parameters     371
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.19863(13) 0.85263(15) 0.34974(5) 0.0262(3) Uani 1 1 d . . .
N2 N 0.6255(7) 0.9783(7) 0.3214(2) 0.0225(10) Uani 0.708(5) 1 d P A 1
N2' N 0.630(2) 0.940(2) 0.3344(6) 0.029(3) Uani 0.292(5) 1 d P A 2
N3 N 0.7693(6) 0.9756(6) 0.4133(2) 0.0289(11) Uani 0.708(5) 1 d P A 1
N3' N 0.7615(18) 1.0268(15) 0.4230(6) 0.037(3) Uani 0.292(5) 1 d P A 2
N4 N 0.6181(9) 1.2693(11) 0.4216(2) 0.0315(12) Uani 0.708(5) 1 d PU A 1
N4' N 0.599(2) 1.288(3) 0.4065(5) 0.040(4) Uani 0.292(5) 1 d PU A 2
C1 C 0.21809(16) 0.99444(18) 0.37623(7) 0.0301(4) Uani 1 1 d . . .
H1 H 0.1620 1.0796 0.3682 0.036 Uiso 1 1 calc R . .
C2 C 0.31150(16) 1.01521(19) 0.41209(6) 0.0294(4) Uani 1 1 d . A .
H2 H 0.3086 1.1149 0.4268 0.035 Uiso 1 1 calc R . .
C3 C 0.41046(16) 0.9198(2) 0.43153(6) 0.0308(4) Uani 1 1 d . A .
H3A H 0.4215 0.8177 0.4192 0.037 Uiso 1 1 calc R . .
H3B H 0.4670 0.9569 0.4571 0.037 Uiso 1 1 calc R . .
C4 C 0.16704(15) 0.86411(18) 0.29992(6) 0.0241(4) Uani 1 1 d . . .
C5 C 0.07529(15) 0.76592(19) 0.27663(7) 0.0281(4) Uani 1 1 d . . .
H5 H 0.0361 0.6842 0.2945 0.034 Uiso 1 1 calc R . .
C6 C 0.04091(16) 0.7859(2) 0.22830(7) 0.0316(4) Uani 1 1 d . . .
H6 H -0.0223 0.7183 0.2134 0.038 Uiso 1 1 calc R . .
C7 C 0.09663(16) 0.9022(2) 0.20115(7) 0.0328(4) Uani 1 1 d . . .
H7 H 0.0726 0.9153 0.1678 0.039 Uiso 1 1 calc R . .
C8 C 0.18816(16) 0.9993(2) 0.22358(7) 0.0338(4) Uani 1 1 d . . .
H8 H 0.2287 1.0788 0.2052 0.041 Uiso 1 1 calc R . .
C9 C 0.22165(16) 0.98273(19) 0.27227(7) 0.0300(4) Uani 1 1 d . . .
H9 H 0.2827 1.0530 0.2872 0.036 Uiso 1 1 calc R . .
C10 C 0.18202(15) 0.71128(18) 0.37482(7) 0.0274(4) Uani 1 1 d . . .
C11 C 0.21600(18) 0.57014(19) 0.35363(7) 0.0379(5) Uani 1 1 d . . .
H11 H 0.2516 0.5691 0.3220 0.045 Uiso 1 1 calc R . .
C12 C 0.1986(2) 0.4325(2) 0.37796(9) 0.0526(6) Uani 1 1 d . . .
H12 H 0.2217 0.3374 0.3629 0.063 Uiso 1 1 calc R . .
C13 C 0.1483(2) 0.4311(2) 0.42382(9) 0.0546(7) Uani 1 1 d . . .
H13 H 0.1342 0.3355 0.4402 0.065 Uiso 1 1 calc R . .
C14 C 0.11840(19) 0.5700(2) 0.44582(8) 0.0461(5) Uani 1 1 d . . .
H14 H 0.0850 0.5701 0.4778 0.055 Uiso 1 1 calc R . .
C15 C 0.13657(16) 0.7100(2) 0.42182(7) 0.0336(4) Uani 1 1 d . . .
H15 H 0.1177 0.8051 0.4377 0.040 Uiso 1 1 calc R . .
C16 C 0.5546(10) 0.8309(13) 0.3175(3) 0.0291(13) Uani 0.708(5) 1 d PU A 1
H16A H 0.4593 0.8507 0.3163 0.044 Uiso 0.708(5) 1 calc PR A 1
H16B H 0.5771 0.7662 0.3459 0.044 Uiso 0.708(5) 1 calc PR A 1
H16C H 0.5799 0.7769 0.2878 0.044 Uiso 0.708(5) 1 calc PR A 1
C16' C 0.543(3) 0.807(4) 0.3160(10) 0.064(6) Uani 0.292(5) 1 d PU A 2
H16D H 0.5302 0.7325 0.3424 0.096 Uiso 0.292(5) 1 calc PR A 2
H16E H 0.5848 0.7553 0.2888 0.096 Uiso 0.292(5) 1 calc PR A 2
H16F H 0.4566 0.8484 0.3051 0.096 Uiso 0.292(5) 1 calc PR A 2
C17 C 0.5900(4) 1.0784(5) 0.27968(18) 0.0439(10) Uani 0.708(5) 1 d P A 1
H17A H 0.4941 1.0940 0.2782 0.066 Uiso 0.708(5) 1 calc PR A 1
H17B H 0.6179 1.0289 0.2496 0.066 Uiso 0.708(5) 1 calc PR A 1
H17C H 0.6343 1.1791 0.2835 0.066 Uiso 0.708(5) 1 calc PR A 1
C17' C 0.6401(12) 1.0410(15) 0.2920(4) 0.046(3) Uani 0.292(5) 1 d P A 2
H17D H 0.5525 1.0823 0.2831 0.069 Uiso 0.292(5) 1 calc PR A 2
H17E H 0.6739 0.9813 0.2647 0.069 Uiso 0.292(5) 1 calc PR A 2
H17F H 0.7004 1.1272 0.2997 0.069 Uiso 0.292(5) 1 calc PR A 2
C18 C 0.7694(2) 0.9554(4) 0.32332(12) 0.0293(8) Uani 0.708(5) 1 d P A 1
H18A H 0.8135 1.0564 0.3181 0.035 Uiso 0.708(5) 1 calc PR A 1
H18B H 0.7943 0.8849 0.2967 0.035 Uiso 0.708(5) 1 calc PR A 1
C18' C 0.7626(7) 0.8784(11) 0.3476(4) 0.035(2) Uani 0.292(5) 1 d P A 2
H18C H 0.8126 0.8595 0.3177 0.042 Uiso 0.292(5) 1 calc PR A 2
H18D H 0.7535 0.7783 0.3649 0.042 Uiso 0.292(5) 1 calc PR A 2
C19 C 0.8176(3) 0.8876(4) 0.37144(13) 0.0308(8) Uani 0.708(5) 1 d P A 1
H19A H 0.7874 0.7785 0.3737 0.037 Uiso 0.708(5) 1 calc PR A 1
H19B H 0.9154 0.8874 0.3726 0.037 Uiso 0.708(5) 1 calc PR A 1
C19' C 0.8367(6) 0.9924(12) 0.3797(3) 0.039(2) Uani 0.292(5) 1 d P A 2
H19C H 0.9236 0.9483 0.3896 0.046 Uiso 0.292(5) 1 calc PR A 2
H19D H 0.8521 1.0895 0.3615 0.046 Uiso 0.292(5) 1 calc PR A 2
C20 C 0.7842(11) 0.8809(17) 0.4581(3) 0.0425(19) Uani 0.708(5) 1 d P A 1
H20A H 0.7394 0.7809 0.4532 0.064 Uiso 0.708(5) 1 calc PR A 1
H20B H 0.7448 0.9360 0.4853 0.064 Uiso 0.708(5) 1 calc PR A 1
H20C H 0.8782 0.8629 0.4654 0.064 Uiso 0.708(5) 1 calc PR A 1
C20' C 0.788(3) 0.918(4) 0.4599(11) 0.057(8) Uani 0.292(5) 1 d P A 2
H20D H 0.7362 0.9434 0.4885 0.086 Uiso 0.292(5) 1 calc PR A 2
H20E H 0.8821 0.9196 0.4688 0.086 Uiso 0.292(5) 1 calc PR A 2
H20F H 0.7634 0.8137 0.4483 0.086 Uiso 0.292(5) 1 calc PR A 2
C21 C 0.8344(3) 1.1272(4) 0.41826(14) 0.0402(9) Uani 0.708(5) 1 d P A 1
H21A H 0.8518 1.1692 0.3855 0.048 Uiso 0.708(5) 1 calc PR A 1
H21B H 0.9203 1.1143 0.4358 0.048 Uiso 0.708(5) 1 calc PR A 1
C21' C 0.7975(10) 1.1786(13) 0.4432(4) 0.044(3) Uani 0.292(5) 1 d P A 2
H21C H 0.8948 1.1900 0.4436 0.053 Uiso 0.292(5) 1 calc PR A 2
H21D H 0.7679 1.1854 0.4771 0.053 Uiso 0.292(5) 1 calc PR A 2
C22 C 0.7499(4) 1.2410(5) 0.44551(17) 0.0414(11) Uani 0.708(5) 1 d P A 1
H22A H 0.7367 1.2008 0.4788 0.050 Uiso 0.708(5) 1 calc PR A 1
H22B H 0.7976 1.3410 0.4485 0.050 Uiso 0.708(5) 1 calc PR A 1
C22' C 0.7361(8) 1.3081(9) 0.4138(4) 0.050(3) Uani 0.292(5) 1 d P A 2
H22C H 0.7526 1.4079 0.4307 0.060 Uiso 0.292(5) 1 calc PR A 2
H22D H 0.7784 1.3134 0.3818 0.060 Uiso 0.292(5) 1 calc PR A 2
C23 C 0.5325(7) 1.3413(9) 0.4574(4) 0.0371(17) Uani 0.708(5) 1 d PU A 1
H23A H 0.5249 1.2722 0.4855 0.056 Uiso 0.708(5) 1 calc PR A 1
H23B H 0.4446 1.3592 0.4427 0.056 Uiso 0.708(5) 1 calc PR A 1
H23C H 0.5706 1.4407 0.4681 0.056 Uiso 0.708(5) 1 calc PR A 1
C23' C 0.530(2) 1.344(2) 0.4486(11) 0.048(5) Uani 0.292(5) 1 d PU A 2
H23D H 0.4344 1.3294 0.4432 0.072 Uiso 0.292(5) 1 calc PR A 2
H23E H 0.5485 1.4549 0.4533 0.072 Uiso 0.292(5) 1 calc PR A 2
H23F H 0.5591 1.2863 0.4776 0.072 Uiso 0.292(5) 1 calc PR A 2
C24 C 0.6323(5) 1.3688(4) 0.37874(14) 0.0510(11) Uani 0.708(5) 1 d P A 1
H24A H 0.6898 1.3177 0.3555 0.077 Uiso 0.708(5) 1 calc PR A 1
H24B H 0.6713 1.4684 0.3887 0.077 Uiso 0.708(5) 1 calc PR A 1
H24C H 0.5453 1.3869 0.3633 0.077 Uiso 0.708(5) 1 calc PR A 1
C24' C 0.5420(13) 1.3918(10) 0.3683(4) 0.068(3) Uani 0.292(5) 1 d P A 2
H24D H 0.4469 1.3727 0.3648 0.102 Uiso 0.292(5) 1 calc PR A 2
H24E H 0.5842 1.3709 0.3373 0.102 Uiso 0.292(5) 1 calc PR A 2
H24F H 0.5573 1.5003 0.3777 0.102 Uiso 0.292(5) 1 calc PR A 2
Li1 Li 0.5710(3) 1.0426(3) 0.39556(11) 0.0283(6) 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
N1 C4 1.402(2) . ?
N1 C10 1.411(2) . ?
N1 C1 1.433(2) . ?
N2 C16 1.460(14) . ?
N2 C18 1.470(8) . ?
N2 C17 1.471(5) . ?
N2 Li1 2.199(7) . ?
N2' C17' 1.458(12) . ?
N2' C18' 1.48(2) . ?
N2' C16' 1.53(4) . ?
N2' Li1 2.005(19) . ?
N3 C21 1.467(7) . ?
N3 C19 1.474(6) . ?
N3 C20 1.480(12) . ?
N3 Li1 2.133(7) . ?
N3' C20' 1.40(3) . ?
N3' C19' 1.459(16) . ?
N3' C21' 1.462(15) . ?
N3' Li1 2.057(18) . ?
N4 C24 1.467(7) . ?
N4 C23 1.469(12) . ?
N4 C22 1.492(9) . ?
N4 Li1 2.128(10) . ?
N4' C22' 1.40(3) . ?
N4' C23' 1.45(3) . ?
N4' C24' 1.487(18) . ?
N4' Li1 2.15(3) . ?
C1 C2 1.360(2) . ?
C2 C3 1.391(2) . ?
C2 Li1 2.690(3) . ?
C3 Li1 2.197(3) . ?
C4 C9 1.396(2) . ?
C4 C5 1.399(2) . ?
C5 C6 1.376(2) . ?
C6 C7 1.380(2) . ?
C7 C8 1.381(2) . ?
C8 C9 1.380(3) . ?
C10 C15 1.384(3) . ?
C10 C11 1.395(2) . ?
C11 C12 1.374(3) . ?
C12 C13 1.373(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.388(3) . ?
C18 C19 1.515(4) . ?
C18' C19' 1.508(12) . ?
C18' Li1 2.764(7) . ?
C19' Li1 2.771(7) . ?
C21 C22 1.513(5) . ?
C21' C22' 1.502(14) . ?

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 C10 120.75(13) . . ?
C4 N1 C1 117.48(13) . . ?
C10 N1 C1 120.20(14) . . ?
C16 N2 C18 111.8(5) . . ?
C16 N2 C17 110.1(6) . . ?
C18 N2 C17 109.2(4) . . ?
C16 N2 Li1 98.7(5) . . ?
C18 N2 Li1 105.8(4) . . ?
C17 N2 Li1 120.9(4) . . ?
C17' N2' C18' 109.3(15) . . ?
C17' N2' C16' 103.5(17) . . ?
C18' N2' C16' 109.0(15) . . ?
C17' N2' Li1 116.0(12) . . ?
C18' N2' Li1 104.0(10) . . ?
C16' N2' Li1 115.0(16) . . ?
C21 N3 C19 111.8(5) . . ?
C21 N3 C20 112.2(7) . . ?
C19 N3 C20 109.8(6) . . ?
C21 N3 Li1 101.4(3) . . ?
C19 N3 Li1 106.9(4) . . ?
C20 N3 Li1 114.4(6) . . ?
C20' N3' C19' 111.2(15) . . ?
C20' N3' C21' 106.4(18) . . ?
C19' N3' C21' 111.1(13) . . ?
C20' N3' Li1 117.8(16) . . ?
C19' N3' Li1 102.7(10) . . ?
C21' N3' Li1 107.6(8) . . ?
C24 N4 C23 111.4(7) . . ?
C24 N4 C22 110.1(6) . . ?
C23 N4 C22 108.1(6) . . ?
C24 N4 Li1 107.0(4) . . ?
C23 N4 Li1 118.8(6) . . ?
C22 N4 Li1 100.8(5) . . ?
C22' N4' C23' 110.1(16) . . ?
C22' N4' C24' 112.9(16) . . ?
C23' N4' C24' 99.9(17) . . ?
C22' N4' Li1 105.7(14) . . ?
C23' N4' Li1 112.0(15) . . ?
C24' N4' Li1 116.4(12) . . ?
C2 C1 N1 124.35(15) . . ?
C1 C2 C3 132.91(16) . . ?
C1 C2 Li1 123.56(14) . . ?
C3 C2 Li1 54.53(11) . . ?
C2 C3 Li1 94.43(13) . . ?
C9 C4 C5 117.43(16) . . ?
C9 C4 N1 120.04(14) . . ?
C5 C4 N1 122.42(15) . . ?
C6 C5 C4 120.98(16) . . ?
C5 C6 C7 121.14(17) . . ?
C6 C7 C8 118.51(17) . . ?
C9 C8 C7 121.00(17) . . ?
C8 C9 C4 120.91(16) . . ?
C15 C10 C11 118.37(17) . . ?
C15 C10 N1 120.71(16) . . ?
C11 C10 N1 120.88(17) . . ?
C12 C11 C10 120.8(2) . . ?
C13 C12 C11 120.7(2) . . ?
C12 C13 C14 119.1(2) . . ?
C13 C14 C15 120.8(2) . . ?
C10 C15 C14 120.18(19) . . ?
N2 C18 C19 112.3(3) . . ?
N2' C18' C19' 110.0(10) . . ?
N2' C18' Li1 44.7(7) . . ?
C19' C18' Li1 74.4(4) . . ?
N3 C19 C18 112.3(3) . . ?
N3' C19' C18' 110.4(9) . . ?
N3' C19' Li1 46.4(8) . . ?
C18' C19' Li1 74.0(4) . . ?
N3 C21 C22 111.3(3) . . ?
N3' C21' C22' 111.3(10) . . ?
N4 C22 C21 113.5(4) . . ?
N4' C22' C21' 112.1(11) . . ?
N2' Li1 N3' 88.8(7) . . ?
N2' Li1 N4 128.0(6) . . ?
N3' Li1 N4 74.8(4) . . ?
N2' Li1 N3 76.9(6) . . ?
N3' Li1 N3 14.1(3) . . ?
N4 Li1 N3 88.3(3) . . ?
N2' Li1 N4' 120.5(7) . . ?
N3' Li1 N4' 83.8(7) . . ?
N4 Li1 N4' 12.8(5) . . ?
N3 Li1 N4' 96.4(7) . . ?
N2' Li1 C3 114.1(6) . . ?
N3' Li1 C3 120.1(5) . . ?
N4 Li1 C3 116.8(3) . . ?
N3 Li1 C3 118.0(2) . . ?
N4' Li1 C3 120.4(6) . . ?
N2' Li1 N2 12.2(4) . . ?
N3' Li1 N2 93.8(5) . . ?
N4 Li1 N2 118.9(3) . . ?
N3 Li1 N2 83.5(3) . . ?
N4' Li1 N2 110.0(5) . . ?
C3 Li1 N2 120.3(2) . . ?
N2' Li1 C2 114.8(6) . . ?
N3' Li1 C2 147.5(5) . . ?
N4 Li1 C2 103.6(3) . . ?
N3 Li1 C2 148.8(2) . . ?
N4' Li1 C2 100.9(7) . . ?
C3 Li1 C2 31.04(7) . . ?
N2 Li1 C2 113.9(2) . . ?
N2' Li1 C18' 31.3(5) . . ?
N3' Li1 C18' 58.5(4) . . ?
N4 Li1 C18' 118.4(3) . . ?
N3 Li1 C18' 45.8(2) . . ?
N4' Li1 C18' 118.4(7) . . ?
C3 Li1 C18' 120.4(3) . . ?
N2 Li1 C18' 39.8(3) . . ?
C2 Li1 C18' 137.5(2) . . ?
N2' Li1 C19' 59.1(6) . . ?
N3' Li1 C19' 30.9(4) . . ?
N4 Li1 C19' 89.2(3) . . ?
N3 Li1 C19' 23.4(3) . . ?
N4' Li1 C19' 92.8(7) . . ?
C3 Li1 C19' 136.8(2) . . ?
N2 Li1 C19' 63.0(3) . . ?
C2 Li1 C19' 166.0(3) . . ?
C18' Li1 C19' 31.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.08
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive, Pyrophoric'
