# 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_qd020615
_database_code_depnum_ccdc_archive 'CCDC 1465290'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_date             2015-06-04T16:40:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C38 H62 Li4 N2 O4'
_chemical_formula_sum            'C38 H62 Li4 N2 O4'
_chemical_formula_weight         638.66
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7871(10)
_cell_length_b                   9.5833(11)
_cell_length_c                   13.1959(13)
_cell_angle_alpha                104.353(4)
_cell_angle_beta                 93.696(4)
_cell_angle_gamma                116.282(4)
_cell_volume                     945.63(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      29.22
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.986


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         micro-source
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_number            23990
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3853
_reflns_number_gt                3319
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0460P)²+0.5119P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3853
_refine_ls_number_parameters     227
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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 0.006 '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'

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
C1 C 0.08593(16) 0.83008(16) 0.27857(10) 0.0198(3) Uani 1 1 d . . .
C2 C 0.15032(18) 0.93600(17) 0.20584(11) 0.0238(3) Uani 1 1 d . . .
H2A H 0.19 0.8938 0.1424 0.029 Uiso 1 1 calc R . .
H2B H 0.0918 1.0005 0.1953 0.029 Uiso 1 1 calc R . .
C3 C 0.25960(17) 0.98641(16) 0.31371(11) 0.0234(3) Uani 1 1 d . . .
H3A H 0.268 1.0817 0.3694 0.028 Uiso 1 1 calc R . .
H3B H 0.3663 0.975 0.3165 0.028 Uiso 1 1 calc R . .
C4 C 0.09739(16) 0.67671(16) 0.24999(10) 0.0190(3) Uani 1 1 d . . .
C5 C 0.01434(17) 0.55588(16) 0.15036(11) 0.0221(3) Uani 1 1 d . . .
H5 H -0.0466 0.5755 0.0981 0.027 Uiso 1 1 calc R . .
C6 C 0.01916(18) 0.40831(17) 0.12639(11) 0.0249(3) Uani 1 1 d . . .
H6 H -0.0383 0.3291 0.0583 0.03 Uiso 1 1 calc R . .
C7 C 0.10662(19) 0.37531(17) 0.20053(12) 0.0265(3) Uani 1 1 d . . .
H7 H 0.1097 0.2744 0.184 0.032 Uiso 1 1 calc R . .
C8 C 0.18977(19) 0.49285(18) 0.29961(12) 0.0269(3) Uani 1 1 d . . .
H8 H 0.2503 0.4721 0.3514 0.032 Uiso 1 1 calc R . .
C9 C 0.18535(18) 0.63993(17) 0.32365(11) 0.0238(3) Uani 1 1 d . . .
H9 H 0.2434 0.7184 0.3919 0.029 Uiso 1 1 calc R . .
C10 C -0.08476(19) 1.11988(17) 0.36647(11) 0.0262(3) Uani 1 1 d . . .
H10A H -0.1494 1.0857 0.2937 0.039 Uiso 1 1 calc R . .
H10B H 0.0383 1.1571 0.3654 0.039 Uiso 1 1 calc R . .
H10C H -0.0989 1.2095 0.4118 0.039 Uiso 1 1 calc R . .
C11 C -0.33437(18) 0.92939(19) 0.40711(12) 0.0260(3) Uani 1 1 d D . .
H11A H -0.386(2) 0.8335(16) 0.4334(14) 0.039 Uiso 1 1 d D . .
H11B H -0.357(2) 1.0157(17) 0.4513(13) 0.039 Uiso 1 1 d D . .
H11C H -0.399(2) 0.902(2) 0.3345(9) 0.039 Uiso 1 1 d D . .
C12 C -0.50597(17) 0.68628(17) 0.11053(11) 0.0233(3) Uani 1 1 d . . .
H12A H -0.5538 0.6725 0.1754 0.028 Uiso 1 1 calc R . .
H12B H -0.5676 0.5808 0.0525 0.028 Uiso 1 1 calc R . .
C13 C -0.5240(2) 0.82040(19) 0.07781(12) 0.0301(3) Uani 1 1 d . . .
H13A H -0.5317 0.8985 0.1397 0.036 Uiso 1 1 calc R . .
H13B H -0.6284 0.7736 0.0213 0.036 Uiso 1 1 calc R . .
C14 C -0.3585(2) 0.90466(18) 0.03594(12) 0.0329(4) Uani 1 1 d . . .
H14A H -0.3866 0.898 -0.0396 0.039 Uiso 1 1 calc R . .
H14B H -0.289 1.0211 0.0792 0.039 Uiso 1 1 calc R . .
C15 C -0.26220(19) 0.80894(19) 0.04706(11) 0.0285(3) Uani 1 1 d . . .
H15A H -0.2894 0.7213 -0.0204 0.034 Uiso 1 1 calc R . .
H15B H -0.1355 0.8821 0.0662 0.034 Uiso 1 1 calc R . .
C16 C -0.2615(2) 0.57255(19) 0.40445(12) 0.0338(4) Uani 1 1 d . . .
H16A H -0.2983 0.6289 0.4634 0.041 Uiso 1 1 calc R . .
H16B H -0.1335 0.6244 0.4195 0.041 Uiso 1 1 calc R . .
C17 C -0.3388(2) 0.39387(19) 0.39353(13) 0.0361(4) Uani 1 1 d . . .
H17A H -0.4542 0.3524 0.4131 0.043 Uiso 1 1 calc R . .
H17B H -0.2623 0.3718 0.4381 0.043 Uiso 1 1 calc R . .
C18 C -0.3525(2) 0.31860(18) 0.27475(12) 0.0321(3) Uani 1 1 d . . .
H18A H -0.24 0.3283 0.2594 0.039 Uiso 1 1 calc R . .
H18B H -0.4415 0.202 0.2487 0.039 Uiso 1 1 calc R . .
C19 C -0.40499(18) 0.42195(16) 0.22575(11) 0.0253(3) Uani 1 1 d . . .
H19A H -0.3638 0.4273 0.158 0.03 Uiso 1 1 calc R . .
H19B H -0.5326 0.3757 0.2111 0.03 Uiso 1 1 calc R . .
N1 N -0.15089(14) 0.98161(14) 0.40900(9) 0.0208(2) Uani 1 1 d . . .
O1 O -0.32258(12) 0.74054(12) 0.13115(7) 0.0240(2) Uani 1 1 d . . .
O2 O -0.32414(12) 0.58247(11) 0.30387(7) 0.0236(2) Uani 1 1 d . . .
Li1 Li 0.0484(3) 0.9345(3) 0.43109(18) 0.0232(5) Uani 1 1 d . . .
Li2 Li -0.1840(3) 0.7884(3) 0.27285(18) 0.0222(5) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C4 1.4744(18) . ?
C1 C2 1.5218(18) . ?
C1 C3 1.5257(18) . ?
C1 Li1 2.131(3) . ?
C1 Li2 2.216(3) . ?
C2 C3 1.5012(19) . ?
C4 C5 1.4054(19) . ?
C4 C9 1.4074(19) . ?
C5 C6 1.3910(19) . ?
C6 C7 1.386(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.385(2) . ?
C10 N1 1.4619(18) . ?
C11 N1 1.4576(17) . ?
C11 Li1 2.757(3) 2_576 ?
C12 O1 1.4396(16) . ?
C12 C13 1.520(2) . ?
C13 C14 1.535(2) . ?
C14 C15 1.523(2) . ?
C15 O1 1.4391(16) . ?
C16 O2 1.4449(17) . ?
C16 C17 1.500(2) . ?
C17 C18 1.526(2) . ?
C18 C19 1.515(2) . ?
C19 O2 1.4441(16) . ?
N1 Li1 2.014(3) . ?
N1 Li1 2.045(3) 2_576 ?
N1 Li2 2.133(3) . ?
O1 Li2 1.994(2) . ?
O2 Li2 1.973(2) . ?
Li1 N1 2.045(3) 2_576 ?
Li1 Li1 2.371(4) 2_576 ?
Li1 Li2 2.441(3) . ?
Li1 C11 2.757(3) 2_576 ?

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 C1 C2 116.04(11) . . ?
C4 C1 C3 115.09(11) . . ?
C2 C1 C3 59.02(9) . . ?
C4 C1 Li1 123.12(11) . . ?
C2 C1 Li1 118.90(11) . . ?
C3 C1 Li1 82.55(10) . . ?
C4 C1 Li2 112.88(10) . . ?
C2 C1 Li2 102.49(10) . . ?
C3 C1 Li2 131.88(11) . . ?
Li1 C1 Li2 68.29(9) . . ?
C3 C2 C1 60.62(9) . . ?
C2 C3 C1 60.36(9) . . ?
C5 C4 C9 116.29(12) . . ?
C5 C4 C1 122.21(12) . . ?
C9 C4 C1 121.42(12) . . ?
C6 C5 C4 121.60(13) . . ?
C7 C6 C5 120.87(13) . . ?
C6 C7 C8 118.62(13) . . ?
C9 C8 C7 120.64(13) . . ?
C8 C9 C4 121.99(13) . . ?
N1 C11 Li1 46.41(8) . 2_576 ?
O1 C12 C13 105.05(11) . . ?
C12 C13 C14 104.22(11) . . ?
C15 C14 C13 103.82(12) . . ?
O1 C15 C14 104.97(11) . . ?
O2 C16 C17 106.34(12) . . ?
C16 C17 C18 101.94(12) . . ?
C19 C18 C17 101.90(12) . . ?
O2 C19 C18 105.52(11) . . ?
C11 N1 C10 107.20(11) . . ?
C11 N1 Li1 147.39(12) . . ?
C10 N1 Li1 104.99(11) . . ?
C11 N1 Li1 102.51(10) . 2_576 ?
C10 N1 Li1 108.71(11) . 2_576 ?
Li1 N1 Li1 71.46(11) . 2_576 ?
C11 N1 Li2 96.80(10) . . ?
C10 N1 Li2 100.69(10) . . ?
Li1 N1 Li2 72.07(9) . . ?
Li1 N1 Li2 137.75(10) 2_576 . ?
C15 O1 C12 104.22(10) . . ?
C15 O1 Li2 127.42(11) . . ?
C12 O1 Li2 124.23(10) . . ?
C19 O2 C16 109.28(10) . . ?
C19 O2 Li2 124.60(10) . . ?
C16 O2 Li2 115.60(11) . . ?
N1 Li1 N1 108.54(11) . 2_576 ?
N1 Li1 C1 108.37(11) . . ?
N1 Li1 C1 142.91(12) 2_576 . ?
N1 Li1 Li1 54.89(9) . 2_576 ?
N1 Li1 Li1 53.65(9) 2_576 2_576 ?
C1 Li1 Li1 162.94(17) . 2_576 ?
N1 Li1 Li2 56.23(8) . . ?
N1 Li1 Li2 155.36(13) 2_576 . ?
C1 Li1 Li2 57.52(8) . . ?
Li1 Li1 Li2 108.18(14) 2_576 . ?
N1 Li1 C11 132.94(11) . 2_576 ?
N1 Li1 C11 31.08(5) 2_576 2_576 ?
C1 Li1 C11 114.00(10) . 2_576 ?
Li1 Li1 C11 80.78(11) 2_576 2_576 ?
Li2 Li1 C11 170.79(12) . 2_576 ?
O2 Li2 O1 99.65(11) . . ?
O2 Li2 N1 106.39(11) . . ?
O1 Li2 N1 122.18(12) . . ?
O2 Li2 C1 109.37(11) . . ?
O1 Li2 C1 117.35(11) . . ?
N1 Li2 C1 101.22(10) . . ?
O2 Li2 Li1 100.59(11) . . ?
O1 Li2 Li1 159.74(13) . . ?
N1 Li2 Li1 51.71(8) . . ?
C1 Li2 Li1 54.20(8) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_QD2050B
_database_code_depnum_ccdc_archive 'CCDC 1465291'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_date             2016-01-11T14:30:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'


# start Validation Reply Form
_vrf_PLAT410_QD2050B             
;
PROBLEM : Short Intra H...H Contact  H23B   ..  H24C    ..       1.85 Ang.  
RESPONSE: The structure presents thermal disorder on one of the THF 
coordinated to a Li. 
This disorder has been well treated with the Part instructions of the 
SHELXL-97 refinement program. 
However, there is still one B alert due to the positions of 
two hydrogen atoms of this THF.

;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C33 H49 Li2 O3'
_chemical_formula_sum            'C33 H49 Li2 O3'
_chemical_formula_weight         507.6
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5802(5)
_cell_length_b                   9.4380(5)
_cell_length_c                   20.2265(11)
_cell_angle_alpha                80.998(2)
_cell_angle_beta                 82.494(2)
_cell_angle_gamma                70.198(2)
_cell_volume                     1516.79(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.32
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             554
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.975

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         micro-source
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_number            27496
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             5557
_reflns_number_gt                4351
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0558P)²+1.2605P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5557
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.134
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
C30 C 0.2130(3) 0.5620(2) 0.82014(13) 0.0349(6) Uani 1 1 d . . .
H30A H 0.2172 0.6069 0.8607 0.042 Uiso 1 1 calc R . .
H30B H 0.1098 0.5352 0.8246 0.042 Uiso 1 1 calc R . .
C29 C 0.2198(3) 0.6718(3) 0.75725(15) 0.0468(7) Uani 1 1 d . . .
H29A H 0.1704 0.65 0.7201 0.056 Uiso 1 1 calc R . .
H29B H 0.1623 0.7783 0.7659 0.056 Uiso 1 1 calc R . .
C28 C 0.4043(3) 0.6401(3) 0.74234(12) 0.0393(6) Uani 1 1 d . . .
H28A H 0.448 0.6899 0.7718 0.047 Uiso 1 1 calc R . .
H28B H 0.4326 0.6737 0.6948 0.047 Uiso 1 1 calc R . .
C27 C 0.4695(3) 0.4692(2) 0.75764(11) 0.0332(5) Uani 1 1 d . . .
H27A H 0.4708 0.4206 0.7175 0.04 Uiso 1 1 calc R . .
H27B H 0.5839 0.4356 0.7719 0.04 Uiso 1 1 calc R . .
C26 C 0.2188(3) 0.2753(3) 0.96233(11) 0.0394(6) Uani 1 1 d . . .
H26A H 0.2572 0.3647 0.952 0.047 Uiso 1 1 calc R A 1
H26B H 0.3043 0.1915 0.9863 0.047 Uiso 1 1 calc R A 1
C25A C 0.0582(6) 0.3128(6) 1.0036(2) 0.0394(7) Uani 0.54 1 d P B 1
H25A H -0.0192 0.4134 0.9877 0.047 Uiso 0.54 1 calc PR B 1
H25B H 0.0726 0.3083 1.0518 0.047 Uiso 0.54 1 calc PR B 1
C24B C 0.0023(6) 0.1827(6) 0.9900(2) 0.0394(7) Uani 0.54 1 d P B 1
H24A H -0.1179 0.2025 1.0027 0.047 Uiso 0.54 1 calc PR B 1
H24B H 0.0661 0.0846 1.0141 0.047 Uiso 0.54 1 calc PR B 1
C24A C -0.0563(7) 0.2600(7) 0.9729(3) 0.0394(7) Uani 0.46 1 d P B 2
H24C H -0.1128 0.37 0.9612 0.047 Uiso 0.46 1 calc PR B 2
H24D H -0.1392 0.2111 0.9938 0.047 Uiso 0.46 1 calc PR B 2
C25B C 0.0796(8) 0.2307(8) 1.0164(3) 0.0394(7) Uani 0.46 1 d P B 2
H25C H 0.1199 0.1229 1.0358 0.047 Uiso 0.46 1 calc PR B 2
H25D H 0.0451 0.2961 1.053 0.047 Uiso 0.46 1 calc PR B 2
C23 C 0.0427(3) 0.1858(3) 0.91261(12) 0.0359(6) Uani 1 1 d . . .
H23A H 0.0648 0.0846 0.8984 0.043 Uiso 1 1 calc R B 1
H23B H -0.0494 0.2605 0.8883 0.043 Uiso 1 1 calc R B 1
C19 C 0.8568(3) -0.0328(3) 0.65219(15) 0.0496(7) Uani 1 1 d . B .
H19A H 0.8154 -0.1148 0.645 0.06 Uiso 1 1 calc R . .
H19B H 0.917 -0.0651 0.6934 0.06 Uiso 1 1 calc R . .
C20 C 0.9660(4) -0.0048(3) 0.59583(16) 0.0561(8) Uani 1 1 d . . .
H20A H 0.9505 -0.0482 0.5566 0.067 Uiso 1 1 calc R . .
H20B H 1.0832 -0.0517 0.6066 0.067 Uiso 1 1 calc R . .
C21 C 0.9235(3) 0.1649(3) 0.58049(12) 0.0371(6) Uani 1 1 d . . .
H21A H 1.0159 0.1977 0.5896 0.044 Uiso 1 1 calc R . .
H21B H 0.8997 0.1987 0.5329 0.044 Uiso 1 1 calc R . .
C22 C 0.7715(3) 0.2278(3) 0.62666(13) 0.0371(6) Uani 1 1 d . B .
H22A H 0.7972 0.281 0.6602 0.045 Uiso 1 1 calc R . .
H22B H 0.6815 0.301 0.6007 0.045 Uiso 1 1 calc R . .
C10 C 0.6051(2) 0.0451(2) 0.83529(10) 0.0213(4) Uani 1 1 d . B .
C11 C 0.6351(3) 0.1299(2) 0.88804(11) 0.0255(5) Uani 1 1 d . B .
H11A H 0.5754 0.2404 0.8859 0.031 Uiso 1 1 calc R . .
H11B H 0.6521 0.0763 0.934 0.031 Uiso 1 1 calc R . .
C12 C 0.7686(3) 0.0752(2) 0.83334(11) 0.0271(5) Uani 1 1 d . . .
H12A H 0.8677 -0.0119 0.8457 0.033 Uiso 1 1 calc R . .
H12B H 0.7911 0.1521 0.7976 0.033 Uiso 1 1 calc R . .
C13 C 0.6092(2) -0.1122(2) 0.85804(9) 0.0191(4) Uani 1 1 d . . .
C14 C 0.4914(2) -0.1465(2) 0.90716(10) 0.0224(4) Uani 1 1 d . . .
H14 H 0.408 -0.0659 0.9269 0.027 Uiso 1 1 calc R . .
C15 C 0.4924(3) -0.2938(2) 0.92777(11) 0.0280(5) Uani 1 1 d . . .
H15 H 0.4108 -0.3123 0.9613 0.034 Uiso 1 1 calc R . .
C16 C 0.6109(3) -0.4142(2) 0.89995(11) 0.0323(5) Uani 1 1 d . . .
H16 H 0.612 -0.5153 0.9141 0.039 Uiso 1 1 calc R . .
C17 C 0.7279(3) -0.3842(2) 0.85101(11) 0.0311(5) Uani 1 1 d . . .
H17 H 0.8096 -0.4658 0.8312 0.037 Uiso 1 1 calc R . .
C18 C 0.7277(2) -0.2372(2) 0.83050(10) 0.0240(5) Uani 1 1 d . . .
H18 H 0.8099 -0.2202 0.7969 0.029 Uiso 1 1 calc R . .
C1 C 0.2956(2) 0.1784(2) 0.72567(9) 0.0195(4) Uani 1 1 d . B .
C3 C 0.2180(3) 0.0584(2) 0.75732(10) 0.0246(5) Uani 1 1 d . B .
H3A H 0.2499 0.006 0.8023 0.03 Uiso 1 1 calc R . .
H3B H 0.1014 0.0757 0.7491 0.03 Uiso 1 1 calc R . .
C2 C 0.3477(3) 0.0250(2) 0.69897(10) 0.0242(5) Uani 1 1 d . . .
H2A H 0.3104 0.0221 0.6551 0.029 Uiso 1 1 calc R . .
H2B H 0.459 -0.0476 0.7083 0.029 Uiso 1 1 calc R . .
C4 C 0.1905(2) 0.3083(2) 0.68367(10) 0.0193(4) Uani 1 1 d . . .
C9 C 0.0304(2) 0.3954(2) 0.70749(10) 0.0238(4) Uani 1 1 d . . .
H9 H -0.0131 0.3671 0.7513 0.029 Uiso 1 1 calc R . .
C8 C -0.0655(3) 0.5215(2) 0.66862(12) 0.0295(5) Uani 1 1 d . . .
H8 H -0.173 0.5782 0.6862 0.035 Uiso 1 1 calc R . .
C7 C -0.0068(3) 0.5654(2) 0.60484(12) 0.0314(5) Uani 1 1 d . . .
H7 H -0.0728 0.6518 0.5784 0.038 Uiso 1 1 calc R . .
C6 C 0.1505(3) 0.4813(2) 0.57980(11) 0.0303(5) Uani 1 1 d . . .
H6 H 0.1921 0.5097 0.5357 0.036 Uiso 1 1 calc R . .
C5 C 0.2471(3) 0.3564(2) 0.61861(10) 0.0248(5) Uani 1 1 d . . .
H5 H 0.355 0.3016 0.6007 0.03 Uiso 1 1 calc R . .
C31 C 0.5416(3) 0.0609(2) 0.49533(11) 0.0260(5) Uani 1 1 d . . .
H31A H 0.5553 0.0831 0.5401 0.031 Uiso 1 1 calc R . .
H31B H 0.6538 0.0212 0.4721 0.031 Uiso 1 1 calc R . .
C32 C 0.4444(3) 0.2073(2) 0.45523(11) 0.0308(5) Uani 1 1 d . . .
H32A H 0.3313 0.246 0.4779 0.037 Uiso 1 1 calc R . .
H32B H 0.433 0.1857 0.4101 0.037 Uiso 1 1 calc R . .
C33 C 0.5268(3) 0.3294(3) 0.44756(13) 0.0422(6) Uani 1 1 d . . .
H33A H 0.534 0.3546 0.492 0.063 Uiso 1 1 calc R . .
H33B H 0.4606 0.4204 0.4206 0.063 Uiso 1 1 calc R . .
H33C H 0.6388 0.2919 0.4251 0.063 Uiso 1 1 calc R . .
Li2 Li 0.3504(4) 0.2193(4) 0.82298(16) 0.0215(7) Uani 1 1 d . . .
Li1 Li 0.5531(4) 0.1082(4) 0.73271(17) 0.0263(8) Uani 1 1 d . B .
O3 O 0.35724(17) 0.43026(15) 0.81135(7) 0.0248(3) Uani 1 1 d . B .
O2 O 0.18937(17) 0.23015(16) 0.90125(7) 0.0251(3) Uani 1 1 d . B .
O1 O 0.72092(17) 0.10315(16) 0.65954(7) 0.0282(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C30 O3 1.442(2) . ?
C30 C29 1.518(4) . ?
C29 C28 1.506(4) . ?
C28 C27 1.513(3) . ?
C27 O3 1.444(3) . ?
C26 O2 1.446(3) . ?
C26 C25A 1.477(5) . ?
C26 C25B 1.629(6) . ?
C25A C24B 1.534(8) . ?
C24B C23 1.556(5) . ?
C24A C25B 1.478(9) . ?
C24A C23 1.514(6) . ?
C23 O2 1.436(3) . ?
C19 O1 1.424(3) . ?
C19 C20 1.429(3) . ?
C20 C21 1.508(3) . ?
C21 C22 1.502(3) . ?
C22 O1 1.429(3) . ?
C10 C13 1.474(3) . ?
C10 C12 1.517(3) . ?
C10 C11 1.524(3) . ?
C10 Li1 2.129(4) . ?
C10 Li2 2.263(4) . ?
C11 C12 1.500(3) . ?
C11 Li2 2.740(4) . ?
C13 C14 1.405(3) . ?
C13 C18 1.407(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.381(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.384(3) . ?
C1 C4 1.471(3) . ?
C1 C3 1.519(3) . ?
C1 C2 1.526(3) . ?
C1 Li1 2.098(4) . ?
C1 Li2 2.201(4) . ?
C3 C2 1.505(3) . ?
C3 Li2 2.748(4) . ?
C2 Li1 2.368(4) . ?
C4 C5 1.403(3) . ?
C4 C9 1.407(3) . ?
C9 C8 1.387(3) . ?
C8 C7 1.376(3) . ?
C7 C6 1.389(3) . ?
C6 C5 1.382(3) . ?
C31 C32 1.519(3) . ?
C31 C31 1.523(4) 2_656 ?
C32 C33 1.524(3) . ?
Li2 O2 1.952(3) . ?
Li2 O3 1.988(3) . ?
Li2 Li1 2.448(5) . ?
Li1 O1 1.920(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C30 C29 105.06(19) . . ?
C28 C29 C30 101.65(19) . . ?
C29 C28 C27 101.55(19) . . ?
O3 C27 C28 105.82(18) . . ?
O2 C26 C25A 106.2(3) . . ?
O2 C26 C25B 102.2(3) . . ?
C25A C26 C25B 27.2(2) . . ?
C26 C25A C24B 98.4(4) . . ?
C25A C24B C23 101.2(3) . . ?
C25B C24A C23 99.7(4) . . ?
C24A C25B C26 100.6(4) . . ?
O2 C23 C24A 106.0(3) . . ?
O2 C23 C24B 102.9(3) . . ?
C24A C23 C24B 29.8(2) . . ?
O1 C19 C20 108.6(2) . . ?
C19 C20 C21 107.0(2) . . ?
C22 C21 C20 104.56(18) . . ?
O1 C22 C21 107.50(18) . . ?
C13 C10 C12 115.95(17) . . ?
C13 C10 C11 115.80(16) . . ?
C12 C10 C11 59.09(13) . . ?
C13 C10 Li1 111.17(16) . . ?
C12 C10 Li1 100.88(16) . . ?
C11 C10 Li1 133.02(17) . . ?
C13 C10 Li2 116.14(15) . . ?
C12 C10 Li2 127.17(16) . . ?
C11 C10 Li2 90.53(14) . . ?
Li1 C10 Li2 67.66(13) . . ?
C12 C11 C10 60.21(13) . . ?
C12 C11 Li2 102.74(14) . . ?
C10 C11 Li2 55.67(12) . . ?
C11 C12 C10 60.70(13) . . ?
C14 C13 C18 115.65(18) . . ?
C14 C13 C10 122.00(17) . . ?
C18 C13 C10 122.32(18) . . ?
C15 C14 C13 122.32(19) . . ?
C16 C15 C14 120.6(2) . . ?
C15 C16 C17 118.6(2) . . ?
C16 C17 C18 121.0(2) . . ?
C17 C18 C13 121.86(19) . . ?
C4 C1 C3 116.30(17) . . ?
C4 C1 C2 116.11(16) . . ?
C3 C1 C2 59.23(13) . . ?
C4 C1 Li1 129.27(17) . . ?
C3 C1 Li1 113.02(16) . . ?
C2 C1 Li1 79.89(15) . . ?
C4 C1 Li2 117.67(15) . . ?
C3 C1 Li2 93.42(14) . . ?
C2 C1 Li2 126.11(16) . . ?
Li1 C1 Li2 69.37(14) . . ?
C2 C3 C1 60.62(13) . . ?
C2 C3 Li2 99.16(14) . . ?
C1 C3 Li2 53.08(12) . . ?
C3 C2 C1 60.15(13) . . ?
C3 C2 Li1 100.76(15) . . ?
C1 C2 Li1 60.71(13) . . ?
C5 C4 C9 116.21(18) . . ?
C5 C4 C1 121.80(17) . . ?
C9 C4 C1 121.93(18) . . ?
C8 C9 C4 121.7(2) . . ?
C7 C8 C9 120.7(2) . . ?
C8 C7 C6 118.9(2) . . ?
C5 C6 C7 120.5(2) . . ?
C6 C5 C4 121.96(19) . . ?
C32 C31 C31 113.2(2) . 2_656 ?
C31 C32 C33 112.77(19) . . ?
O2 Li2 O3 99.42(15) . . ?
O2 Li2 C1 120.98(17) . . ?
O3 Li2 C1 106.69(16) . . ?
O2 Li2 C10 116.13(16) . . ?
O3 Li2 C10 112.04(16) . . ?
C1 Li2 C10 101.50(14) . . ?
O2 Li2 Li1 158.65(19) . . ?
O3 Li2 Li1 101.88(16) . . ?
C1 Li2 Li1 53.32(12) . . ?
C10 Li2 Li1 53.57(12) . . ?
O2 Li2 C11 98.81(14) . . ?
O3 Li2 C11 88.29(13) . . ?
C1 Li2 C11 133.17(15) . . ?
C10 Li2 C11 33.80(8) . . ?
Li1 Li2 C11 80.50(13) . . ?
O2 Li2 C3 94.39(13) . . ?
O3 Li2 C3 135.65(16) . . ?
C1 Li2 C3 33.50(8) . . ?
C10 Li2 C3 98.72(13) . . ?
Li1 Li2 C3 71.17(13) . . ?
C11 Li2 C3 130.90(13) . . ?
O1 Li1 C1 126.50(19) . . ?
O1 Li1 C10 123.75(18) . . ?
C1 Li1 C10 109.74(16) . . ?
O1 Li1 C2 108.55(17) . . ?
C1 Li1 C2 39.40(9) . . ?
C10 Li1 C2 115.97(17) . . ?
O1 Li1 Li2 156.0(2) . . ?
C1 Li1 Li2 57.31(12) . . ?
C10 Li1 Li2 58.76(12) . . ?
C2 Li1 Li2 87.72(14) . . ?
C30 O3 C27 109.06(16) . . ?
C30 O3 Li2 123.95(16) . . ?
C27 O3 Li2 117.18(15) . . ?
C23 O2 C26 109.42(16) . . ?
C23 O2 Li2 130.22(16) . . ?
C26 O2 Li2 120.10(16) . . ?
C19 O1 C22 108.11(17) . . ?
C19 O1 Li1 119.82(17) . . ?
C22 O1 Li1 126.84(17) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
