# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_2198

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 Dilithium fumarate
;
_chemical_name_common            'Lithium fumarate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 Li2 O4'
_chemical_formula_sum            'C4 H2 Li2 O4'
_chemical_formula_weight         127.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Li Li -0.0003 0.0001 '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'
C C 0.0033 0.0016 '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_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic

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

_cell_length_a                   3.3392(3)
_cell_length_b                   4.9297(3)
_cell_length_c                   7.4736(5)
_cell_angle_alpha                76.777(5)
_cell_angle_beta                 86.619(6)
_cell_angle_gamma                78.680(6)
_cell_volume                     117.421(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    120
_cell_measurement_reflns_used    1861
_cell_measurement_theta_min      4.3153
_cell_measurement_theta_max      29.3201

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             64
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_min  0.77994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1183
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3120
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0100
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.32
_diffrn_reflns_theta_max         29.38
_reflns_number_total             586
_reflns_number_gt                558
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    Sir-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep & Mercury'
_computing_publication_material  ?

_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 > 2σ(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)+(0.0472P)²+0.0336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         586
_refine_ls_number_parameters     49
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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 0.89721(18) -0.18475(13) 0.71909(8) 0.0098(2) Uani 1 1 d . . .
O2 O 0.59625(19) 0.27147(13) 0.64509(8) 0.0099(2) Uani 1 1 d . . .
C1 C 0.7996(2) 0.06094(18) 0.75257(11) 0.0081(2) Uani 1 1 d . . .
C2 C 0.9194(3) 0.10644(17) 0.93227(11) 0.0089(2) Uani 1 1 d . . .
H1 H 0.867(4) 0.297(3) 0.9457(17) 0.011 Uiso 1 1 d . . .
Li1 Li 0.4499(5) 0.6788(3) 0.6228(2) 0.0123(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0109(3) 0.0086(3) 0.0104(3) -0.0034(2) -0.0007(2) -0.0015(2)
O2 0.0117(3) 0.0089(3) 0.0084(3) -0.0011(2) -0.0020(2) -0.0005(2)
C1 0.0071(4) 0.0097(4) 0.0078(4) -0.0018(3) 0.0008(3) -0.0029(3)
C2 0.0096(4) 0.0090(4) 0.0087(4) -0.0032(3) -0.0005(3) -0.0021(3)
Li1 0.0141(7) 0.0115(7) 0.0115(7) -0.0041(6) -0.0012(6) -0.0011(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.2688(10) . ?
O1 Li1 1.9858(17) 1_545 ?
O1 Li1 1.9884(17) 1_645 ?
O2 C1 1.2608(10) . ?
O2 Li1 1.9416(17) . ?
O2 Li1 1.9724(17) 2_666 ?
C1 C2 1.5002(11) . ?
C1 Li1 2.7722(17) 1_545 ?
C2 C2 1.3313(16) 2_757 ?
Li1 O2 1.9724(17) 2_666 ?
Li1 O1 1.9858(17) 1_565 ?
Li1 O1 1.9884(17) 1_465 ?
Li1 C1 2.7722(17) 1_565 ?
Li1 Li1 2.787(3) 2_666 ?
Li1 Li1 3.3392(3) 1_455 ?
Li1 Li1 3.3392(3) 1_655 ?
Li1 Li1 3.346(3) 2_676 ?

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 O1 Li1 115.03(7) . 1_545 ?
C1 O1 Li1 121.32(7) . 1_645 ?
Li1 O1 Li1 114.32(8) 1_545 1_645 ?
C1 O2 Li1 137.45(7) . . ?
C1 O2 Li1 126.25(7) . 2_666 ?
Li1 O2 Li1 90.80(7) . 2_666 ?
O2 C1 O1 123.88(8) . . ?
O2 C1 C2 117.08(7) . . ?
O1 C1 C2 119.01(8) . . ?
O2 C1 Li1 92.63(6) . 1_545 ?
O1 C1 Li1 40.47(5) . 1_545 ?
C2 C1 Li1 138.93(7) . 1_545 ?
C2 C2 C1 122.63(10) 2_757 . ?
O2 Li1 O2 89.20(7) . 2_666 ?
O2 Li1 O1 109.62(8) . 1_565 ?
O2 Li1 O1 119.10(8) 2_666 1_565 ?
O2 Li1 O1 115.19(8) . 1_465 ?
O2 Li1 O1 107.15(8) 2_666 1_465 ?
O1 Li1 O1 114.32(8) 1_565 1_465 ?
O2 Li1 C1 132.91(8) . 1_565 ?
O2 Li1 C1 118.58(7) 2_666 1_565 ?
O1 Li1 C1 24.50(3) 1_565 1_565 ?
O1 Li1 C1 93.28(6) 1_465 1_565 ?
O2 Li1 Li1 45.04(5) . 2_666 ?
O2 Li1 Li1 44.16(5) 2_666 2_666 ?
O1 Li1 Li1 125.32(10) 1_565 2_666 ?
O1 Li1 Li1 120.35(10) 1_465 2_666 ?
C1 Li1 Li1 144.38(10) 1_565 2_666 ?
O2 Li1 Li1 93.08(5) . 1_455 ?
O2 Li1 Li1 83.47(5) 2_666 1_455 ?
O1 Li1 Li1 147.14(5) 1_565 1_455 ?
O1 Li1 Li1 32.81(5) 1_465 1_455 ?
C1 Li1 Li1 125.11(4) 1_565 1_455 ?
Li1 Li1 Li1 87.54(7) 2_666 1_455 ?
O2 Li1 Li1 86.92(5) . 1_655 ?
O2 Li1 Li1 96.53(5) 2_666 1_655 ?
O1 Li1 Li1 32.86(5) 1_565 1_655 ?
O1 Li1 Li1 147.19(5) 1_465 1_655 ?
C1 Li1 Li1 54.89(4) 1_565 1_655 ?
Li1 Li1 Li1 92.46(7) 2_666 1_655 ?
Li1 Li1 Li1 180.00(11) 1_455 1_655 ?
O2 Li1 Li1 146.46(10) . 2_676 ?
O2 Li1 Li1 65.42(6) 2_666 2_676 ?
O1 Li1 Li1 69.08(6) 1_565 2_676 ?
O1 Li1 Li1 93.95(7) 1_465 2_676 ?
C1 Li1 Li1 55.68(5) 1_565 2_676 ?
Li1 Li1 Li1 106.64(10) 2_666 2_676 ?
Li1 Li1 Li1 104.68(5) 1_455 2_676 ?
Li1 Li1 Li1 75.32(5) 1_655 2_676 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Li1 O2 C1 O1 -169.11(9) . . . . ?
Li1 O2 C1 O1 -23.56(13) 2_666 . . . ?
Li1 O2 C1 C2 12.73(14) . . . . ?
Li1 O2 C1 C2 158.28(8) 2_666 . . . ?
Li1 O2 C1 Li1 163.32(12) . . . 1_545 ?
Li1 O2 C1 Li1 -51.13(10) 2_666 . . 1_545 ?
Li1 O1 C1 O2 -45.42(11) 1_545 . . . ?
Li1 O1 C1 O2 99.29(10) 1_645 . . . ?
Li1 O1 C1 C2 132.70(8) 1_545 . . . ?
Li1 O1 C1 C2 -82.59(10) 1_645 . . . ?
Li1 O1 C1 Li1 144.71(13) 1_645 . . 1_545 ?
O2 C1 C2 C2 169.90(10) . . . 2_757 ?
O1 C1 C2 C2 -8.35(15) . . . 2_757 ?
Li1 C1 C2 C2 38.21(17) 1_545 . . 2_757 ?
C1 O2 Li1 O2 152.85(10) . . . 2_666 ?
Li1 O2 Li1 O2 0.0 2_666 . . 2_666 ?
C1 O2 Li1 O1 32.09(14) . . . 1_565 ?
Li1 O2 Li1 O1 -120.76(10) 2_666 . . 1_565 ?
C1 O2 Li1 O1 -98.52(12) . . . 1_465 ?
Li1 O2 Li1 O1 108.62(10) 2_666 . . 1_465 ?
C1 O2 Li1 C1 23.04(16) . . . 1_565 ?
Li1 O2 Li1 C1 -129.81(13) 2_666 . . 1_565 ?
C1 O2 Li1 Li1 152.85(10) . . . 2_666 ?
C1 O2 Li1 Li1 -123.73(10) . . . 1_455 ?
Li1 O2 Li1 Li1 83.42(5) 2_666 . . 1_455 ?
C1 O2 Li1 Li1 56.27(10) . . . 1_655 ?
Li1 O2 Li1 Li1 -96.58(5) 2_666 . . 1_655 ?
C1 O2 Li1 Li1 113.56(17) . . . 2_676 ?
Li1 O2 Li1 Li1 -39.29(14) 2_666 . . 2_676 ?

_diffrn_measured_fraction_theta_max 0.897
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 1018021'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_2866

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 Dilithium (L-malate)0.43 (fumarate)0.57
;
_chemical_name_common            'Lithium malate : fumarate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration syn
_chemical_formula_sum            'C4 H2.85 Li2 O4.43'
_chemical_formula_weight         135.60

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'

_symmetry_space_group_name_H-M   'R 3'
_symmetry_cell_setting           TRIGONAL

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

_cell_length_a                   11.8093(10)
_cell_length_b                   11.8093(10)
_cell_length_c                   10.9615(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1323.9(2)
_cell_formula_units_Z            9
_cell_measurement_temperature    119.95(10)
_cell_measurement_reflns_used    427
_cell_measurement_theta_min      3.4434
_cell_measurement_theta_max      28.6171

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             614
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_min  0.60576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      119.95(10)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1330
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         28.68
_reflns_number_total             936
_reflns_number_gt                696
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond, Mercury'
_computing_publication_material  ?

_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 > 2σ(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)+(0.0720P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(5)
_refine_ls_number_reflns         936
_refine_ls_number_parameters     107
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
O4 O 0.7573(4) -0.0391(4) 0.1458(3) 0.0333(10) Uani 1 1 d . . .
C1 C 0.8248(6) 0.2558(7) -0.1387(6) 0.0366(16) Uani 1 1 d . . .
O1 O 0.9049(4) 0.3741(4) -0.1306(3) 0.0331(10) Uani 1 1 d . . .
O2 O 0.7679(4) 0.1983(4) -0.2342(4) 0.0356(11) Uani 1 1 d . A .
Li2 Li 0.7443(10) -0.1682(11) 0.2651(10) 0.034(3) Uani 1 1 d . . .
C3A C 0.8674(16) 0.1777(13) 0.0544(13) 0.0456(19) Uani 0.575(12) 1 d P A 1
H3A H 0.9357 0.2625 0.0671 0.055 Uiso 0.575(12) 1 calc PR A 1
C2A C 0.8050(14) 0.1560(13) -0.0441(12) 0.0456(19) Uani 0.575(12) 1 d P A 1
H2A H 0.7407 0.0701 -0.0595 0.055 Uiso 0.575(12) 1 calc PR A 1
C2B C 0.7844(17) 0.1936(17) -0.0049(16) 0.0340(19) Uani 0.425(12) 1 d P A 2
H2B H 0.6963 0.1176 -0.0125 0.041 Uiso 0.425(12) 1 calc PR A 2
C3B C 0.8756(17) 0.1392(19) 0.0218(18) 0.0340(19) Uani 0.425(12) 1 d P A 2
H3B1 H 0.9663 0.2083 0.0173 0.041 Uiso 0.425(12) 1 calc PR A 2
H3B2 H 0.8616 0.0719 -0.0369 0.041 Uiso 0.425(12) 1 calc PR A 2
O5 O 0.7770(12) 0.2696(10) 0.0827(8) 0.086(5) Uani 0.425(12) 1 d P A 2
H5 H 0.7263 0.2941 0.0612 0.128 Uiso 0.425(12) 1 calc PR A 2
O3 O 0.9043(4) 0.1345(4) 0.2493(3) 0.0316(9) Uani 1 1 d . . .
Li1 Li 0.8293(9) 0.0831(10) 0.4076(10) 0.031(2) Uani 1 1 d . . .
C4 C 0.8423(6) 0.0813(6) 0.1520(5) 0.0302(14) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.035(3) 0.031(3) 0.032(2) 0.002(2) -0.0024(19) 0.015(2)
C1 0.024(3) 0.039(4) 0.040(4) 0.015(3) 0.000(3) 0.011(3)
O1 0.029(2) 0.037(3) 0.027(2) 0.000(2) -0.0041(17) 0.012(2)
O2 0.030(2) 0.032(2) 0.035(2) -0.0017(17) -0.003(2) 0.0081(18)
Li2 0.041(6) 0.044(7) 0.022(5) 0.003(4) -0.008(4) 0.025(5)
C3A 0.050(3) 0.030(3) 0.033(4) 0.001(2) -0.021(3) 0.002(2)
C2A 0.050(3) 0.030(3) 0.033(4) 0.001(2) -0.021(3) 0.002(2)
C2B 0.035(3) 0.039(4) 0.024(4) 0.000(3) 0.005(3) 0.015(3)
C3B 0.035(3) 0.039(4) 0.024(4) 0.000(3) 0.005(3) 0.015(3)
O5 0.146(11) 0.111(9) 0.052(7) 0.018(5) 0.015(6) 0.103(9)
O3 0.034(2) 0.036(2) 0.0210(19) 0.0042(17) 0.0008(19) 0.0146(18)
Li1 0.026(5) 0.029(5) 0.040(6) 0.011(4) 0.009(4) 0.014(4)
C4 0.031(3) 0.039(4) 0.020(3) 0.001(2) -0.002(2) 0.017(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O4 C4 1.268(7) . ?
O4 Li2 1.957(11) . ?
O4 Li1 1.962(11) 9_654 ?
C1 O1 1.238(8) . ?
C1 O2 1.246(8) . ?
C1 C2A 1.498(13) . ?
C1 C2B 1.603(17) . ?
O1 Li2 1.947(11) 7_554 ?
O1 Li1 2.022(12) 6_664 ?
O2 Li1 1.931(11) 5_544 ?
O2 Li2 1.965(12) 5_544 ?
Li2 O3 1.913(12) 2_645 ?
Li2 O1 1.947(11) 4_445 ?
Li2 O2 1.965(12) 9_655 ?
Li2 Li1 2.819(7) 9_654 ?
Li2 Li1 3.046(17) . ?
Li2 Li1 3.110(15) 2_645 ?
C3A C2A 1.259(11) . ?
C3A C4 1.480(13) . ?
C2B O5 1.35(2) . ?
C2B C3B 1.533(16) . ?
C3B C4 1.546(19) . ?
O3 C4 1.268(7) . ?
O3 Li1 1.905(12) . ?
O3 Li2 1.913(12) 3_765 ?
Li1 O2 1.931(11) 9_655 ?
Li1 O4 1.962(11) 5_545 ?
Li1 O1 2.022(12) 8_645 ?
Li1 Li2 2.819(7) 5_545 ?
Li1 Li2 3.110(15) 3_765 ?

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 O4 Li2 123.2(5) . . ?
C4 O4 Li1 143.0(5) . 9_654 ?
Li2 O4 Li1 92.0(5) . 9_654 ?
O1 C1 O2 125.1(6) . . ?
O1 C1 C2A 124.7(7) . . ?
O2 C1 C2A 108.9(8) . . ?
O1 C1 C2B 109.6(9) . . ?
O2 C1 C2B 124.2(9) . . ?
C2A C1 C2B 27.3(7) . . ?
C1 O1 Li2 142.9(5) . 7_554 ?
C1 O1 Li1 122.3(5) . 6_664 ?
Li2 O1 Li1 90.5(4) 7_554 6_664 ?
C1 O2 Li1 128.3(6) . 5_544 ?
C1 O2 Li2 126.7(5) . 5_544 ?
Li1 O2 Li2 102.9(6) 5_544 5_544 ?
O3 Li2 O1 112.5(6) 2_645 4_445 ?
O3 Li2 O4 117.1(6) 2_645 . ?
O1 Li2 O4 89.8(5) 4_445 . ?
O3 Li2 O2 106.3(5) 2_645 9_655 ?
O1 Li2 O2 119.9(6) 4_445 9_655 ?
O4 Li2 O2 111.3(6) . 9_655 ?
O3 Li2 Li1 124.7(4) 2_645 9_654 ?
O1 Li2 Li1 45.8(3) 4_445 9_654 ?
O4 Li2 Li1 44.1(3) . 9_654 ?
O2 Li2 Li1 129.0(4) 9_655 9_654 ?
O3 Li2 Li1 118.3(5) 2_645 . ?
O1 Li2 Li1 128.7(6) 4_445 . ?
O4 Li2 Li1 74.0(5) . . ?
O2 Li2 Li1 38.2(2) 9_655 . ?
Li1 Li2 Li1 104.9(3) 9_654 . ?
O3 Li2 Li1 35.4(4) 2_645 2_645 ?
O1 Li2 Li1 122.8(5) 4_445 2_645 ?
O4 Li2 Li1 141.3(6) . 2_645 ?
O2 Li2 Li1 72.5(3) 9_655 2_645 ?
Li1 Li2 Li1 157.9(3) 9_654 2_645 ?
Li1 Li2 Li1 96.3(4) . 2_645 ?
C2A C3A C4 126.3(8) . . ?
C3A C2A C1 126.0(8) . . ?
O5 C2B C3B 115.9(12) . . ?
O5 C2B C1 116.8(12) . . ?
C3B C2B C1 104.9(10) . . ?
C2B C3B C4 106.5(10) . . ?
C4 O3 Li1 123.2(5) . . ?
C4 O3 Li2 127.2(5) . 3_765 ?
Li1 O3 Li2 109.1(6) . 3_765 ?
O3 Li1 O2 110.4(6) . 9_655 ?
O3 Li1 O4 124.6(6) . 5_545 ?
O2 Li1 O4 108.9(5) 9_655 5_545 ?
O3 Li1 O1 110.2(5) . 8_645 ?
O2 Li1 O1 113.4(6) 9_655 8_645 ?
O4 Li1 O1 87.5(5) 5_545 8_645 ?
O3 Li1 Li2 127.6(4) . 5_545 ?
O2 Li1 Li2 121.6(4) 9_655 5_545 ?
O4 Li1 Li2 43.9(3) 5_545 5_545 ?
O1 Li1 Li2 43.7(3) 8_645 5_545 ?
O3 Li1 Li2 73.6(3) . . ?
O2 Li1 Li2 39.0(4) 9_655 . ?
O4 Li1 Li2 123.3(5) 5_545 . ?
O1 Li1 Li2 141.1(6) 8_645 . ?
Li2 Li1 Li2 158.3(3) 5_545 . ?
O3 Li1 Li2 35.5(2) . 3_765 ?
O2 Li1 Li2 121.2(5) 9_655 3_765 ?
O4 Li1 Li2 129.8(5) 5_545 3_765 ?
O1 Li1 Li2 75.2(4) 8_645 3_765 ?
Li2 Li1 Li2 104.2(3) 5_545 3_765 ?
Li2 Li1 Li2 96.8(5) . 3_765 ?
O3 C4 O4 122.6(6) . . ?
O3 C4 C3A 112.5(7) . . ?
O4 C4 C3A 124.4(7) . . ?
O3 C4 C3B 127.0(10) . . ?
O4 C4 C3B 109.2(10) . . ?
C3A C4 C3B 23.7(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 O1 Li2 -131.0(8) . . . 7_554 ?
C2A C1 O1 Li2 34.1(17) . . . 7_554 ?
C2B C1 O1 Li2 60.0(13) . . . 7_554 ?
O2 C1 O1 Li1 17.6(11) . . . 6_664 ?
C2A C1 O1 Li1 -177.3(11) . . . 6_664 ?
C2B C1 O1 Li1 -151.4(8) . . . 6_664 ?
O1 C1 O2 Li1 -131.0(6) . . . 5_544 ?
C2A C1 O2 Li1 61.9(11) . . . 5_544 ?
C2B C1 O2 Li1 36.4(13) . . . 5_544 ?
O1 C1 O2 Li2 29.5(10) . . . 5_544 ?
C2A C1 O2 Li2 -137.7(9) . . . 5_544 ?
C2B C1 O2 Li2 -163.1(9) . . . 5_544 ?
C4 O4 Li2 O3 -79.1(8) . . . 2_645 ?
Li1 O4 Li2 O3 113.0(5) 9_654 . . 2_645 ?
C4 O4 Li2 O1 165.5(4) . . . 4_445 ?
Li1 O4 Li2 O1 -2.4(7) 9_654 . . 4_445 ?
C4 O4 Li2 O2 43.3(8) . . . 9_655 ?
Li1 O4 Li2 O2 -124.6(4) 9_654 . . 9_655 ?
C4 O4 Li2 Li1 167.9(8) . . . 9_654 ?
C4 O4 Li2 Li1 34.9(6) . . . . ?
Li1 O4 Li2 Li1 -133.0(4) 9_654 . . . ?
C4 O4 Li2 Li1 -44.9(10) . . . 2_645 ?
Li1 O4 Li2 Li1 147.2(6) 9_654 . . 2_645 ?
C4 C3A C2A C1 175.6(19) . . . . ?
O1 C1 C2A C3A -1(2) . . . . ?
O2 C1 C2A C3A 166.0(15) . . . . ?
C2B C1 C2A C3A -65(2) . . . . ?
O1 C1 C2B O5 35.2(15) . . . . ?
O2 C1 C2B O5 -133.9(12) . . . . ?
C2A C1 C2B O5 164(3) . . . . ?
O1 C1 C2B C3B -94.6(11) . . . . ?
O2 C1 C2B C3B 96.3(11) . . . . ?
C2A C1 C2B C3B 34.1(17) . . . . ?
O5 C2B C3B C4 48.2(15) . . . . ?
C1 C2B C3B C4 178.5(14) . . . . ?
C4 O3 Li1 O2 56.2(7) . . . 9_655 ?
Li2 O3 Li1 O2 -115.6(7) 3_765 . . 9_655 ?
C4 O3 Li1 O4 -76.4(9) . . . 5_545 ?
Li2 O3 Li1 O4 111.8(6) 3_765 . . 5_545 ?
C4 O3 Li1 O1 -177.8(5) . . . 8_645 ?
Li2 O3 Li1 O1 10.4(6) 3_765 . . 8_645 ?
C4 O3 Li1 Li2 -131.4(5) . . . 5_545 ?
Li2 O3 Li1 Li2 56.8(5) 3_765 . . 5_545 ?
C4 O3 Li1 Li2 43.1(6) . . . . ?
Li2 O3 Li1 Li2 -128.7(5) 3_765 . . . ?
C4 O3 Li1 Li2 171.8(7) . . . 3_765 ?
O3 Li2 Li1 O3 80.1(4) 2_645 . . . ?
O1 Li2 Li1 O3 -108.9(7) 4_445 . . . ?
O4 Li2 Li1 O3 -32.4(4) . . . . ?
O2 Li2 Li1 O3 160.3(4) 9_655 . . . ?
Li1 Li2 Li1 O3 -64.2(3) 9_654 . . . ?
Li1 Li2 Li1 O3 109.3(3) 2_645 . . . ?
O3 Li2 Li1 O2 -80.2(6) 2_645 . . 9_655 ?
O1 Li2 Li1 O2 90.8(5) 4_445 . . 9_655 ?
O4 Li2 Li1 O2 167.3(5) . . . 9_655 ?
Li1 Li2 Li1 O2 135.5(4) 9_654 . . 9_655 ?
Li1 Li2 Li1 O2 -50.9(4) 2_645 . . 9_655 ?
O3 Li2 Li1 O4 -158.9(8) 2_645 . . 5_545 ?
O1 Li2 Li1 O4 12.1(7) 4_445 . . 5_545 ?
O4 Li2 Li1 O4 88.5(4) . . . 5_545 ?
O2 Li2 Li1 O4 -78.8(7) 9_655 . . 5_545 ?
Li1 Li2 Li1 O4 56.8(6) 9_654 . . 5_545 ?
Li1 Li2 Li1 O4 -129.7(7) 2_645 . . 5_545 ?
O3 Li2 Li1 O1 -21.8(9) 2_645 . . 8_645 ?
O1 Li2 Li1 O1 149.2(7) 4_445 . . 8_645 ?
O4 Li2 Li1 O1 -134.4(8) . . . 8_645 ?
O2 Li2 Li1 O1 58.3(7) 9_655 . . 8_645 ?
Li1 Li2 Li1 O1 -166.1(6) 9_654 . . 8_645 ?
Li1 Li2 Li1 O1 7.4(8) 2_645 . . 8_645 ?
O3 Li2 Li1 Li2 -111.7(10) 2_645 . . 5_545 ?
O1 Li2 Li1 Li2 59.3(11) 4_445 . . 5_545 ?
O4 Li2 Li1 Li2 135.8(7) . . . 5_545 ?
O2 Li2 Li1 Li2 -31.5(9) 9_655 . . 5_545 ?
Li1 Li2 Li1 Li2 104.0(9) 9_654 . . 5_545 ?
Li1 Li2 Li1 Li2 -82.5(10) 2_645 . . 5_545 ?
O3 Li2 Li1 Li2 52.9(4) 2_645 . . 3_765 ?
O1 Li2 Li1 Li2 -136.0(6) 4_445 . . 3_765 ?
O4 Li2 Li1 Li2 -59.6(5) . . . 3_765 ?
O2 Li2 Li1 Li2 133.1(5) 9_655 . . 3_765 ?
Li1 Li2 Li1 Li2 -91.3(3) 9_654 . . 3_765 ?
Li1 Li2 Li1 Li2 82.2(3) 2_645 . . 3_765 ?
Li1 O3 C4 O4 -34.2(9) . . . . ?
Li2 O3 C4 O4 136.1(6) 3_765 . . . ?
Li1 O3 C4 C3A 138.1(10) . . . . ?
Li2 O3 C4 C3A -51.6(11) 3_765 . . . ?
Li1 O3 C4 C3B 159.9(10) . . . . ?
Li2 O3 C4 C3B -29.8(13) 3_765 . . . ?
Li2 O4 C4 O3 -18.1(10) . . . . ?
Li1 O4 C4 O3 141.6(7) 9_654 . . . ?
Li2 O4 C4 C3A 170.6(12) . . . . ?
Li1 O4 C4 C3A -29.8(16) 9_654 . . . ?
Li2 O4 C4 C3B 150.1(9) . . . . ?
Li1 O4 C4 C3B -50.3(12) 9_654 . . . ?
C2A C3A C4 O3 -168.4(15) . . . . ?
C2A C3A C4 O4 4(2) . . . . ?
C2A C3A C4 C3B 59(2) . . . . ?
C2B C3B C4 O3 -100.1(11) . . . . ?
C2B C3B C4 O4 92.4(11) . . . . ?
C2B C3B C4 C3A -42(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.862
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 1018022'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_2891

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Lithium malate : fumarate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2.44 Li2 O4.22'
_chemical_formula_sum            'C4 H2.44 Li2 O4.22'
_chemical_formula_weight         131.90

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'

_symmetry_space_group_name_H-M   'R 3'
_symmetry_cell_setting           TRIGONAL

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

_cell_length_a                   11.7600(6)
_cell_length_b                   11.7600(6)
_cell_length_c                   11.0689(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1325.71(13)
_cell_formula_units_Z            9
_cell_measurement_temperature    120.00(10)
_cell_measurement_reflns_used    822
_cell_measurement_theta_min      3.4579
_cell_measurement_theta_max      29.2281

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_min  0.80749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120.00(10)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2127
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         29.29
_reflns_number_total             1273
_reflns_number_gt                994
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond and Mercury'

_computing_publication_material  ?

_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 > 2σ(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)+(0.0677P)²+0.5189P] 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(4)
_refine_ls_number_reflns         1273
_refine_ls_number_parameters     113
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.042
_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
O2 O 0.4646(4) 0.0927(4) 0.9198(3) 0.0311(8) Uani 1 1 d . A .
O1 O 0.4339(5) 0.2343(4) 0.8138(3) 0.0325(9) Uani 1 1 d . . .
C1 C 0.4274(6) 0.1736(6) 0.9093(5) 0.0308(12) Uani 1 1 d D . .
Li1 Li 0.4226(10) -0.0773(10) 0.9843(8) 0.030(2) Uani 1 1 d . . .
C2A C 0.3552(10) 0.2015(8) 1.0108(8) 0.039(2) Uani 0.772(8) 1 d P A 1
H2A H 0.3395 0.2709 0.9996 0.046 Uiso 0.772(8) 1 calc PR A 1
Li2 Li 0.5814(11) 0.0792(10) 0.7955(10) 0.035(2) Uani 1 1 d . . .
C3A C 0.3153(11) 0.1368(10) 1.1088(8) 0.045(2) Uani 0.772(8) 1 d P A 1
H3A H 0.3345 0.0699 1.1209 0.055 Uiso 0.772(8) 1 calc PR A 1
C4 C 0.2424(6) 0.1583(6) 1.2039(5) 0.0306(12) Uani 1 1 d D . .
O3 O 0.2025(4) 0.2405(4) 1.1949(3) 0.0310(8) Uani 1 1 d . . .
O4 O 0.2335(5) 0.0976(4) 1.3001(3) 0.0327(9) Uani 1 1 d . . .
C3 C 0.269(3) 0.128(3) 1.0730(19) 0.036(3) Uani 0.228(8) 1 d PD A 2
H3A H 0.2409 0.0349 1.0668 0.044 Uiso 0.228(8) 1 calc PR A 2
H3B H 0.2182 0.1465 1.0160 0.044 Uiso 0.228(8) 1 calc PR A 2
C2 C 0.412(3) 0.207(3) 1.0402(18) 0.036(3) Uani 0.228(8) 1 d PD A 2
H2 H 0.4273 0.2965 1.0340 0.044 Uiso 0.228(8) 1 calc PR A 2
O5 O 0.4899(13) 0.2152(18) 1.1307(11) 0.090(6) Uani 0.228(8) 1 d P A 2
H5 H 0.4457 0.1640 1.1843 0.136 Uiso 0.228(8) 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.033(2) 0.028(2) 0.032(2) 0.0062(17) 0.0056(18) 0.0146(19)
O1 0.042(2) 0.028(2) 0.031(2) 0.0007(16) -0.0021(18) 0.0200(19)
C1 0.032(3) 0.028(3) 0.028(3) 0.001(2) 0.012(2) 0.012(2)
Li1 0.027(5) 0.037(5) 0.024(5) 0.002(4) 0.004(4) 0.014(4)
C2A 0.063(6) 0.031(3) 0.040(4) 0.015(3) 0.028(4) 0.037(4)
Li2 0.035(5) 0.030(5) 0.040(5) 0.009(4) 0.000(4) 0.016(4)
C3A 0.065(6) 0.065(5) 0.028(4) 0.015(4) 0.005(4) 0.048(5)
C4 0.036(3) 0.022(3) 0.030(3) -0.001(2) 0.002(2) 0.012(2)
O3 0.037(2) 0.032(2) 0.027(2) 0.0001(17) 0.0008(18) 0.018(2)
O4 0.043(2) 0.030(2) 0.027(2) 0.0007(16) 0.0058(18) 0.0191(19)
C3 0.040(7) 0.039(4) 0.040(5) 0.001(4) -0.003(4) 0.027(5)
C2 0.040(7) 0.039(4) 0.040(5) 0.001(4) -0.003(4) 0.027(5)
O5 0.064(8) 0.166(17) 0.052(8) -0.014(8) 0.000(6) 0.065(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O2 C1 1.236(7) . ?
O2 Li1 1.939(10) . ?
O2 Li2 2.005(12) . ?
O1 C1 1.257(8) . ?
O1 Li2 1.917(12) 3_665 ?
O1 Li1 1.934(10) 8_544 ?
C1 C2 1.535(17) . ?
C1 C2A 1.540(8) . ?
Li1 O1 1.934(10) 6 ?
Li1 O4 1.938(11) 8_544 ?
Li1 O3 1.973(11) 7_544 ?
Li1 Li2 2.793(5) . ?
Li1 Li2 3.059(16) 5_545 ?
Li1 Li2 3.117(16) 6 ?
C2A C3A 1.273(6) . ?
Li2 O1 1.917(12) 2_655 ?
Li2 O4 1.943(11) 6_554 ?
Li2 O3 1.957(10) 7_544 ?
Li2 Li1 3.059(16) 9_654 ?
Li2 Li1 3.117(16) 8_544 ?
C3A C4 1.458(9) . ?
C4 O4 1.257(8) . ?
C4 O3 1.272(7) . ?
C4 C3 1.564(16) . ?
O3 Li2 1.957(10) 4_455 ?
O3 Li1 1.973(11) 4_455 ?
O4 Li1 1.938(11) 6 ?
O4 Li2 1.943(11) 8_545 ?
C3 C2 1.504(15) . ?
C2 O5 1.32(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
C1 O2 Li1 145.3(5) . . ?
C1 O2 Li2 121.1(5) . . ?
Li1 O2 Li2 90.1(4) . . ?
C1 O1 Li2 127.6(5) . 3_665 ?
C1 O1 Li1 126.5(5) . 8_544 ?
Li2 O1 Li1 105.2(6) 3_665 8_544 ?
O2 C1 O1 124.9(5) . . ?
O2 C1 C2 103.8(13) . . ?
O1 C1 C2 129.1(13) . . ?
O2 C1 C2A 122.8(6) . . ?
O1 C1 C2A 112.1(6) . . ?
C2 C1 C2A 27.1(10) . . ?
O1 Li1 O4 106.1(5) 6 8_544 ?
O1 Li1 O2 122.8(5) 6 . ?
O4 Li1 O2 109.0(5) 8_544 . ?
O1 Li1 O3 112.7(5) 6 7_544 ?
O4 Li1 O3 115.8(5) 8_544 7_544 ?
O2 Li1 O3 90.3(4) . 7_544 ?
O1 Li1 Li2 130.6(4) 6 . ?
O4 Li1 Li2 123.1(3) 8_544 . ?
O2 Li1 Li2 45.9(3) . . ?
O3 Li1 Li2 44.5(3) 7_544 . ?
O1 Li1 Li2 37.2(2) 6 5_545 ?
O4 Li1 Li2 119.1(6) 8_544 5_545 ?
O2 Li1 Li2 131.3(5) . 5_545 ?
O3 Li1 Li2 76.0(4) 7_544 5_545 ?
Li2 Li1 Li2 106.6(3) . 5_545 ?
O1 Li1 Li2 71.1(3) 6 6 ?
O4 Li1 Li2 36.6(4) 8_544 6 ?
O2 Li1 Li2 121.1(5) . 6 ?
O3 Li1 Li2 141.2(6) 7_544 6 ?
Li2 Li1 Li2 157.4(3) . 6 ?
Li2 Li1 Li2 95.3(5) 5_545 6 ?
C3A C2A C1 124.9(5) . . ?
O1 Li2 O4 108.0(5) 2_655 6_554 ?
O1 Li2 O3 110.4(5) 2_655 7_544 ?
O4 Li2 O3 122.1(6) 6_554 7_544 ?
O1 Li2 O2 115.8(6) 2_655 . ?
O4 Li2 O2 111.0(6) 6_554 . ?
O3 Li2 O2 88.9(4) 7_544 . ?
O1 Li2 Li1 123.0(4) 2_655 . ?
O4 Li2 Li1 128.8(4) 6_554 . ?
O3 Li2 Li1 44.9(3) 7_544 . ?
O2 Li2 Li1 44.0(3) . . ?
O1 Li2 Li1 37.6(4) 2_655 9_654 ?
O4 Li2 Li1 72.4(3) 6_554 9_654 ?
O3 Li2 Li1 121.9(5) 7_544 9_654 ?
O2 Li2 Li1 142.5(6) . 9_654 ?
Li1 Li2 Li1 157.8(3) . 9_654 ?
O1 Li2 Li1 119.2(5) 2_655 8_544 ?
O4 Li2 Li1 36.5(2) 6_554 8_544 ?
O3 Li2 Li1 130.1(5) 7_544 8_544 ?
O2 Li2 Li1 75.3(4) . 8_544 ?
Li1 Li2 Li1 105.8(3) . 8_544 ?
Li1 Li2 Li1 95.9(5) 9_654 8_544 ?
C2A C3A C4 125.7(5) . . ?
O4 C4 O3 122.7(5) . . ?
O4 C4 C3A 113.7(6) . . ?
O3 C4 C3A 123.3(6) . . ?
O4 C4 C3 128.5(13) . . ?
O3 C4 C3 107.3(12) . . ?
C3A C4 C3 24.0(10) . . ?
C4 O3 Li2 143.1(5) . 4_455 ?
C4 O3 Li1 122.6(5) . 4_455 ?
Li2 O3 Li1 90.6(5) 4_455 4_455 ?
C4 O4 Li1 126.9(5) . 6 ?
C4 O4 Li2 125.4(5) . 8_545 ?
Li1 O4 Li2 106.8(5) 6 8_545 ?
C2 C3 C4 111.9(16) . . ?
O5 C2 C3 112.3(19) . . ?
O5 C2 C1 125(2) . . ?
C3 C2 C1 107.8(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Li1 O2 C1 O1 -136.2(7) . . . . ?
Li2 O2 C1 O1 15.2(9) . . . . ?
Li1 O2 C1 C2 59.2(17) . . . . ?
Li2 O2 C1 C2 -149.4(13) . . . . ?
Li1 O2 C1 C2A 37.9(13) . . . . ?
Li2 O2 C1 C2A -170.7(7) . . . . ?
Li2 O1 C1 O2 -132.9(7) 3_665 . . . ?
Li1 O1 C1 O2 35.4(11) 8_544 . . . ?
Li2 O1 C1 C2 27.7(18) 3_665 . . . ?
Li1 O1 C1 C2 -164.0(16) 8_544 . . . ?
Li2 O1 C1 C2A 52.5(9) 3_665 . . . ?
Li1 O1 C1 C2A -139.3(6) 8_544 . . . ?
C1 O2 Li1 O1 -87.1(10) . . . 6 ?
Li2 O2 Li1 O1 117.1(5) . . . 6 ?
C1 O2 Li1 O4 37.7(11) . . . 8_544 ?
Li2 O2 Li1 O4 -118.1(4) . . . 8_544 ?
C1 O2 Li1 O3 155.3(8) . . . 7_544 ?
Li2 O2 Li1 O3 -0.5(6) . . . 7_544 ?
C1 O2 Li1 Li2 155.8(11) . . . . ?
C1 O2 Li1 Li2 -133.1(9) . . . 5_545 ?
Li2 O2 Li1 Li2 71.1(5) . . . 5_545 ?
C1 O2 Li1 Li2 -0.7(11) . . . 6 ?
Li2 O2 Li1 Li2 -156.5(2) . . . 6 ?
O2 C1 C2A C3A -7.4(12) . . . . ?
O1 C1 C2A C3A 167.4(7) . . . . ?
C2 C1 C2A C3A -58(3) . . . . ?
C1 O2 Li2 O1 84.1(7) . . . 2_655 ?
Li1 O2 Li2 O1 -111.7(5) . . . 2_655 ?
C1 O2 Li2 O4 -39.5(7) . . . 6_554 ?
Li1 O2 Li2 O4 124.7(4) . . . 6_554 ?
C1 O2 Li2 O3 -163.7(5) . . . 7_544 ?
Li1 O2 Li2 O3 0.5(6) . . . 7_544 ?
C1 O2 Li2 Li1 -164.2(7) . . . . ?
C1 O2 Li2 Li1 48.8(10) . . . 9_654 ?
Li1 O2 Li2 Li1 -147.1(6) . . . 9_654 ?
C1 O2 Li2 Li1 -31.5(6) . . . 8_544 ?
Li1 O2 Li2 Li1 132.7(4) . . . 8_544 ?
O1 Li1 Li2 O1 -5.0(5) 6 . . 2_655 ?
O4 Li1 Li2 O1 179.1(8) 8_544 . . 2_655 ?
O2 Li1 Li2 O1 94.3(7) . . . 2_655 ?
O3 Li1 Li2 O1 -86.4(6) 7_544 . . 2_655 ?
Li2 Li1 Li2 O1 -37.9(3) 5_545 . . 2_655 ?
Li2 Li1 Li2 O1 157.1(10) 6 . . 2_655 ?
O1 Li1 Li2 O4 -179.4(8) 6 . . 6_554 ?
O4 Li1 Li2 O4 4.7(4) 8_544 . . 6_554 ?
O2 Li1 Li2 O4 -80.1(6) . . . 6_554 ?
O3 Li1 Li2 O4 99.2(7) 7_544 . . 6_554 ?
Li2 Li1 Li2 O4 147.7(7) 5_545 . . 6_554 ?
Li2 Li1 Li2 O4 -17.3(8) 6 . . 6_554 ?
O1 Li1 Li2 O3 81.4(6) 6 . . 7_544 ?
O4 Li1 Li2 O3 -94.5(6) 8_544 . . 7_544 ?
O2 Li1 Li2 O3 -179.3(9) . . . 7_544 ?
Li2 Li1 Li2 O3 48.5(6) 5_545 . . 7_544 ?
Li2 Li1 Li2 O3 -116.5(11) 6 . . 7_544 ?
O1 Li1 Li2 O2 -99.3(7) 6 . . . ?
O4 Li1 Li2 O2 84.8(6) 8_544 . . . ?
O3 Li1 Li2 O2 179.3(9) 7_544 . . . ?
Li2 Li1 Li2 O2 -132.2(5) 5_545 . . . ?
Li2 Li1 Li2 O2 62.8(7) 6 . . . ?
O1 Li1 Li2 Li1 19.7(8) 6 . . 9_654 ?
O4 Li1 Li2 Li1 -156.2(11) 8_544 . . 9_654 ?
O2 Li1 Li2 Li1 119.0(11) . . . 9_654 ?
O3 Li1 Li2 Li1 -61.7(7) 7_544 . . 9_654 ?
Li2 Li1 Li2 Li1 -13.2(7) 5_545 . . 9_654 ?
Li2 Li1 Li2 Li1 -178.2(15) 6 . . 9_654 ?
O1 Li1 Li2 Li1 -147.0(7) 6 . . 8_544 ?
O4 Li1 Li2 Li1 37.1(3) 8_544 . . 8_544 ?
O2 Li1 Li2 Li1 -47.7(5) . . . 8_544 ?
O3 Li1 Li2 Li1 131.6(5) 7_544 . . 8_544 ?
Li2 Li1 Li2 Li1 -179.8(5) 5_545 . . 8_544 ?
Li2 Li1 Li2 Li1 15.1(7) 6 . . 8_544 ?
C1 C2A C3A C4 -177.5(12) . . . . ?
C2A C3A C4 O4 -168.6(7) . . . . ?
C2A C3A C4 O3 4.9(12) . . . . ?
C2A C3A C4 C3 58(3) . . . . ?
O4 C4 O3 Li2 137.7(7) . . . 4_455 ?
C3A C4 O3 Li2 -35.2(12) . . . 4_455 ?
C3 C4 O3 Li2 -55.0(17) . . . 4_455 ?
O4 C4 O3 Li1 -13.2(9) . . . 4_455 ?
C3A C4 O3 Li1 173.9(8) . . . 4_455 ?
C3 C4 O3 Li1 154.0(13) . . . 4_455 ?
O3 C4 O4 Li1 132.0(6) . . . 6 ?
C3A C4 O4 Li1 -54.4(9) . . . 6 ?
C3 C4 O4 Li1 -32.3(18) . . . 6 ?
O3 C4 O4 Li2 -35.9(10) . . . 8_545 ?
C3A C4 O4 Li2 137.6(6) . . . 8_545 ?
C3 C4 O4 Li2 159.8(16) . . . 8_545 ?
O4 C4 C3 C2 -95.8(16) . . . . ?
O3 C4 C3 C2 97.9(14) . . . . ?
C3A C4 C3 C2 -38(3) . . . . ?
C4 C3 C2 O5 41.1(19) . . . . ?
C4 C3 C2 C1 -178(2) . . . . ?
O2 C1 C2 O5 36(3) . . . . ?
O1 C1 C2 O5 -128(2) . . . . ?
C2A C1 C2 O5 174(6) . . . . ?
O2 C1 C2 C3 -99.0(13) . . . . ?
O1 C1 C2 C3 97.3(16) . . . . ?
C2A C1 C2 C3 39(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.873
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 1018023'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_2910

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Lithium malate : fumarate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2.40 Li2 O4.20'
_chemical_formula_sum            'C4 H2.40 Li2 O4.20'
_chemical_formula_weight         131.54

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'

_symmetry_space_group_name_H-M   'R 3'
_symmetry_cell_setting           TRIGONAL

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

_cell_length_a                   11.7253(15)
_cell_length_b                   11.7253(15)
_cell_length_c                   11.126(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1324.7(4)
_cell_formula_units_Z            9
_cell_measurement_temperature    120
_cell_measurement_reflns_used    589
_cell_measurement_theta_min      3.4681
_cell_measurement_theta_max      28.9680

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_min  0.39656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1652
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         29.03
_reflns_number_total             1067
_reflns_number_gt                835
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond and Mercury'
_computing_publication_material  ?

_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 > 2σ(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)+(0.1803P)²+0.6300P] 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   -3(5)
_refine_ls_number_reflns         1067
_refine_ls_number_parameters     101
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0847
_refine_ls_wR_factor_ref         0.2582
_refine_ls_wR_factor_gt          0.2339
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_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 0.7049(5) 0.1302(6) 0.4774(4) 0.0389(13) Uani 1 1 d . A .
O4 O 0.5332(6) 0.1009(5) 0.5834(4) 0.0368(12) Uani 1 1 d . . .
C6 C 0.4844(10) 0.0126(13) 0.3901(11) 0.0442(14) Uani 0.800(14) 1 d P A 1
H6 H 0.3971 -0.0103 0.4029 0.053 Uiso 0.800(14) 1 calc PR A 1
C7 C 0.5823(7) 0.0909(8) 0.4859(6) 0.0368(16) Uani 1 1 d D . .
Li8 Li 0.8325(15) 0.2457(15) 0.6015(11) 0.050(4) Uani 1 1 d . . .
C1 C 0.5120(10) -0.0247(12) 0.2923(10) 0.0442(14) Uani 0.800(14) 1 d P A 1
H1 H 0.5971 -0.0099 0.2828 0.053 Uiso 0.800(14) 1 calc PR A 1
C3 C 0.4142(9) -0.0921(8) 0.1895(6) 0.0392(18) Uani 1 1 d D . .
O2 O 0.2965(5) -0.1305(5) 0.2029(3) 0.0374(13) Uani 1 1 d D . .
O3 O 0.4690(6) -0.0997(6) 0.0952(5) 0.0424(13) Uani 1 1 d D A .
Li1 Li 0.5891(10) -0.1649(10) 0.0801(10) 0.033(3) Uani 1 1 d . . .
C2 C 0.512(4) 0.064(4) 0.367(2) 0.0442(14) Uani 0.200(14) 1 d PD A 2
H2 H 0.4443 0.0896 0.3701 0.053 Uiso 0.200(14) 1 calc PR A 2
C4 C 0.457(3) -0.071(3) 0.3187(17) 0.0442(14) Uani 0.200(14) 1 d PD A 2
H4A H 0.3825 -0.1301 0.3677 0.053 Uiso 0.200(14) 1 calc PR A 2
H4B H 0.5236 -0.0971 0.3282 0.053 Uiso 0.200(14) 1 calc PR A 2
O6 O 0.611(5) 0.137(6) 0.264(3) 0.16(3) Uani 0.200(14) 1 d P A 2
H6A H 0.6847 0.1830 0.2923 0.234 Uiso 0.200(14) 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.045(3) 0.043(3) 0.033(3) -0.002(2) 0.001(2) 0.026(3)
O4 0.042(3) 0.050(3) 0.019(2) -0.005(2) -0.0034(19) 0.024(3)
C6 0.032(2) 0.059(3) 0.039(2) -0.015(2) -0.0023(16) 0.021(2)
C7 0.036(4) 0.044(4) 0.032(4) -0.006(3) -0.006(3) 0.022(3)
Li8 0.054(8) 0.072(9) 0.033(7) 0.002(6) 0.020(5) 0.039(7)
C1 0.032(2) 0.059(3) 0.039(2) -0.015(2) -0.0023(16) 0.021(2)
C3 0.053(5) 0.048(4) 0.026(4) -0.009(3) -0.008(3) 0.032(4)
O2 0.038(3) 0.044(3) 0.028(3) -0.004(2) -0.001(2) 0.019(2)
O3 0.039(3) 0.050(3) 0.047(3) 0.001(2) 0.002(2) 0.028(3)
Li1 0.042(6) 0.034(5) 0.034(7) 0.014(4) 0.012(4) 0.028(5)
C2 0.032(2) 0.059(3) 0.039(2) -0.015(2) -0.0023(16) 0.021(2)
C4 0.032(2) 0.059(3) 0.039(2) -0.015(2) -0.0023(16) 0.021(2)
O6 0.13(3) 0.20(5) 0.045(18) 0.01(2) 0.00(2) 0.01(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.274(10) . ?
O1 Li1 1.927(12) 5_545 ?
O1 Li8 1.987(17) . ?
O4 C7 1.261(9) . ?
O4 Li8 1.931(15) 3_665 ?
O4 Li1 1.955(13) 9_655 ?
C6 C1 1.272(8) . ?
C6 C7 1.498(12) . ?
C7 C2 1.502(19) . ?
Li8 O3 1.920(13) 9_655 ?
Li8 O4 1.931(15) 2_655 ?
Li8 O2 1.973(13) 4 ?
Li8 Li1 2.793(10) 5_545 ?
Li8 Li1 3.076(18) 9_655 ?
Li8 Li1 3.10(2) 7 ?
C1 C3 1.530(11) . ?
C3 O2 1.229(10) . ?
C3 O3 1.257(10) . ?
C3 C4 1.503(16) . ?
O2 Li8 1.973(13) 7_444 ?
O2 Li1 1.998(11) 2_545 ?
O3 Li1 1.916(10) . ?
O3 Li8 1.920(13) 5_544 ?
Li1 O1 1.927(12) 9_654 ?
Li1 O4 1.954(13) 5_544 ?
Li1 O2 1.998(11) 3_655 ?
Li1 Li8 2.793(10) 9_654 ?
Li1 Li8 3.076(18) 5_544 ?
Li1 Li8 3.10(2) 4_444 ?
C2 C4 1.485(19) . ?
C2 O6 1.55(6) . ?

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
C7 O1 Li1 144.0(6) . 5_545 ?
C7 O1 Li8 121.6(6) . . ?
Li1 O1 Li8 91.0(5) 5_545 . ?
C7 O4 Li8 125.9(6) . 3_665 ?
C7 O4 Li1 128.0(5) . 9_655 ?
Li8 O4 Li1 105.6(6) 3_665 9_655 ?
C1 C6 C7 124.8(7) . . ?
O4 C7 O1 121.0(6) . . ?
O4 C7 C6 115.1(7) . . ?
O1 C7 C6 123.3(7) . . ?
O4 C7 C2 123.1(17) . . ?
O1 C7 C2 114.3(18) . . ?
C6 C7 C2 22.4(15) . . ?
O3 Li8 O4 107.6(6) 9_655 2_655 ?
O3 Li8 O2 121.9(8) 9_655 4 ?
O4 Li8 O2 109.0(7) 2_655 4 ?
O3 Li8 O1 112.6(8) 9_655 . ?
O4 Li8 O1 116.1(8) 2_655 . ?
O2 Li8 O1 89.3(5) 4 . ?
O3 Li8 Li1 129.6(6) 9_655 5_545 ?
O4 Li8 Li1 122.7(4) 2_655 5_545 ?
O2 Li8 Li1 45.7(4) 4 5_545 ?
O1 Li8 Li1 43.6(3) . 5_545 ?
O3 Li8 Li1 36.7(3) 9_655 9_655 ?
O4 Li8 Li1 119.6(6) 2_655 9_655 ?
O2 Li8 Li1 130.8(7) 4 9_655 ?
O1 Li8 Li1 76.8(5) . 9_655 ?
Li1 Li8 Li1 106.6(4) 5_545 9_655 ?
O3 Li8 Li1 71.9(4) 9_655 7 ?
O4 Li8 Li1 37.5(4) 2_655 7 ?
O2 Li8 Li1 120.5(7) 4 7 ?
O1 Li8 Li1 143.0(7) . 7 ?
Li1 Li8 Li1 157.3(4) 5_545 7 ?
Li1 Li8 Li1 95.6(5) 9_655 7 ?
C6 C1 C3 124.3(7) . . ?
O2 C3 O3 126.5(7) . . ?
O2 C3 C4 99.8(12) . . ?
O3 C3 C4 131.9(13) . . ?
O2 C3 C1 120.9(7) . . ?
O3 C3 C1 112.6(8) . . ?
C4 C3 C1 25.3(11) . . ?
C3 O2 Li8 145.6(6) . 7_444 ?
C3 O2 Li1 120.7(6) . 2_545 ?
Li8 O2 Li1 89.4(6) 7_444 2_545 ?
C3 O3 Li1 127.2(6) . . ?
C3 O3 Li8 125.2(7) . 5_544 ?
Li1 O3 Li8 106.6(7) . 5_544 ?
O3 Li1 O1 110.0(6) . 9_654 ?
O3 Li1 O4 105.7(6) . 5_544 ?
O1 Li1 O4 122.7(5) 9_654 5_544 ?
O3 Li1 O2 116.4(6) . 3_655 ?
O1 Li1 O2 90.3(5) 9_654 3_655 ?
O4 Li1 O2 112.0(5) 5_544 3_655 ?
O3 Li1 Li8 123.7(5) . 9_654 ?
O1 Li1 Li8 45.3(4) 9_654 9_654 ?
O4 Li1 Li8 130.5(4) 5_544 9_654 ?
O2 Li1 Li8 44.9(4) 3_655 9_654 ?
O3 Li1 Li8 36.7(4) . 5_544 ?
O1 Li1 Li8 121.7(5) 9_654 5_544 ?
O4 Li1 Li8 70.6(4) 5_544 5_544 ?
O2 Li1 Li8 141.4(6) 3_655 5_544 ?
Li8 Li1 Li8 158.0(4) 9_654 5_544 ?
O3 Li1 Li8 118.1(7) . 4_444 ?
O1 Li1 Li8 131.3(5) 9_654 4_444 ?
O4 Li1 Li8 36.9(3) 5_544 4_444 ?
O2 Li1 Li8 75.7(4) 3_655 4_444 ?
Li8 Li1 Li8 107.0(4) 9_654 4_444 ?
Li8 Li1 Li8 94.4(6) 5_544 4_444 ?
C4 C2 C7 116(2) . . ?
C4 C2 O6 97(3) . . ?
C7 C2 O6 111(3) . . ?
C2 C4 C3 117.0(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Li8 O4 C7 O1 133.4(8) 3_665 . . . ?
Li1 O4 C7 O1 -37.2(11) 9_655 . . . ?
Li8 O4 C7 C6 -55.3(12) 3_665 . . . ?
Li1 O4 C7 C6 134.1(8) 9_655 . . . ?
Li8 O4 C7 C2 -31(2) 3_665 . . . ?
Li1 O4 C7 C2 158.1(18) 9_655 . . . ?
Li1 O1 C7 O4 137.9(8) 5_545 . . . ?
Li8 O1 C7 O4 -14.4(11) . . . . ?
Li1 O1 C7 C6 -32.7(16) 5_545 . . . ?
Li8 O1 C7 C6 175.1(10) . . . . ?
Li1 O1 C7 C2 -56(2) 5_545 . . . ?
Li8 O1 C7 C2 151.6(16) . . . . ?
C1 C6 C7 O4 -169.6(9) . . . . ?
C1 C6 C7 O1 1.4(16) . . . . ?
C1 C6 C7 C2 74(4) . . . . ?
C7 O1 Li8 O3 39.8(10) . . . 9_655 ?
Li1 O1 Li8 O3 -124.3(6) 5_545 . . 9_655 ?
C7 O1 Li8 O4 -84.9(8) . . . 2_655 ?
Li1 O1 Li8 O4 111.0(6) 5_545 . . 2_655 ?
C7 O1 Li8 O2 164.3(5) . . . 4 ?
Li1 O1 Li8 O2 0.2(7) 5_545 . . 4 ?
C7 O1 Li8 Li1 164.1(8) . . . 5_545 ?
C7 O1 Li8 Li1 31.9(7) . . . 9_655 ?
Li1 O1 Li8 Li1 -132.2(4) 5_545 . . 9_655 ?
C7 O1 Li8 Li1 -49.8(12) . . . 7 ?
Li1 O1 Li8 Li1 146.0(8) 5_545 . . 7 ?
C7 C6 C1 C3 -173.4(14) . . . . ?
C6 C1 C3 O2 -10.0(15) . . . . ?
C6 C1 C3 O3 168.7(9) . . . . ?
C6 C1 C3 C4 -47(3) . . . . ?
O3 C3 O2 Li8 -135.3(9) . . . 7_444 ?
C4 C3 O2 Li8 58.4(19) . . . 7_444 ?
C1 C3 O2 Li8 43.3(16) . . . 7_444 ?
O3 C3 O2 Li1 12.4(12) . . . 2_545 ?
C4 C3 O2 Li1 -153.9(13) . . . 2_545 ?
C1 C3 O2 Li1 -169.0(8) . . . 2_545 ?
O2 C3 O3 Li1 -131.0(9) . . . . ?
C4 C3 O3 Li1 31(2) . . . . ?
C1 C3 O3 Li1 50.3(11) . . . . ?
O2 C3 O3 Li8 36.0(13) . . . 5_544 ?
C4 C3 O3 Li8 -162.3(18) . . . 5_544 ?
C1 C3 O3 Li8 -142.7(8) . . . 5_544 ?
C3 O3 Li1 O1 -74.3(9) . . . 9_654 ?
Li8 O3 Li1 O1 116.7(7) 5_544 . . 9_654 ?
C3 O3 Li1 O4 151.3(7) . . . 5_544 ?
Li8 O3 Li1 O4 -17.7(6) 5_544 . . 5_544 ?
C3 O3 Li1 O2 26.4(10) . . . 3_655 ?
Li8 O3 Li1 O2 -142.6(7) 5_544 . . 3_655 ?
C3 O3 Li1 Li8 -25.4(9) . . . 9_654 ?
Li8 O3 Li1 Li8 165.6(5) 5_544 . . 9_654 ?
C3 O3 Li1 Li8 169.0(10) . . . 5_544 ?
C3 O3 Li1 Li8 113.7(7) . . . 4_444 ?
Li8 O3 Li1 Li8 -55.3(7) 5_544 . . 4_444 ?
O4 C7 C2 C4 -105(3) . . . . ?
O1 C7 C2 C4 89(3) . . . . ?
C6 C7 C2 C4 -30(3) . . . . ?
O4 C7 C2 O6 145(3) . . . . ?
O1 C7 C2 O6 -20(4) . . . . ?
C6 C7 C2 O6 -140(6) . . . . ?
C7 C2 C4 C3 -167(2) . . . . ?
O6 C2 C4 C3 -49(4) . . . . ?
O2 C3 C4 C2 -95(3) . . . . ?
O3 C3 C4 C2 100(3) . . . . ?
C1 C3 C4 C2 54(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.881
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.079
_database_code_depnum_ccdc_archive 'CCDC 1018024'
