#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/52/2235278.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235278
loop_
_publ_author_name
'Allen, Joshua L.'
'Paillard, Elie'
'Boyle, Paul D.'
'Henderson, Wesley A.'
_publ_section_title
;
 Lithium bis(2-methyllactato)borate monohydrate
;
_journal_coeditor_code           VN2036
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m749
_journal_paper_doi               10.1107/S1600536812017540
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Li (C8 H12 B O6) (H2 O)]'
_chemical_formula_moiety         'C8 H14 B Li O7'
_chemical_formula_sum            'C8 H14 B Li O7'
_chemical_formula_weight         239.94
_chemical_name_systematic
;
poly[[aqualithium(I)]-μ-3,3,8,8-tetramethyl-1,4,6,9-tetraoxa-5λ⁴-
borataspiro[4.4]nonane-2,7-dione]
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7034(4)
_cell_length_b                   11.3939(4)
_cell_length_c                   15.8258(5)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    110
_cell_measurement_theta_max      35.02
_cell_measurement_theta_min      2.72
_cell_volume                     2290.65(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'cif2tables.py (Boyle, 2008)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      110
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker--Nonius Kappa X8 APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            97648
_diffrn_reflns_theta_full        35.90
_diffrn_reflns_theta_max         37.41
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         5663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0519P)²+0.3146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                4436
_reflns_number_total             5663
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vn2036.cif
_cod_data_source_block           I
_cod_database_code               2235278
_cod_database_fobs_code          2235278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Li Li1 0.50924(9) 0.90999(11) 0.30769(8) 0.0141(2) Uani d 1 1
O O1 0.36589(3) 0.97594(4) 0.31383(3) 0.01110(9) Uani d 1 1
O O2 0.21632(3) 1.07434(4) 0.36227(3) 0.01158(9) Uani d 1 1
O O3 0.09643(4) 1.00827(4) 0.27079(3) 0.01399(9) Uani d 1 1
O O4 0.38947(4) 1.16989(4) 0.37533(3) 0.01216(9) Uani d 1 1
O O5 0.34797(4) 1.01520(4) 0.46522(3) 0.01186(9) Uani d 1 1
O O6 0.42797(4) 1.07518(5) 0.58279(3) 0.01560(10) Uani d 1 1
B B1 0.33286(5) 1.05967(6) 0.37751(4) 0.01016(11) Uani d 1 1
C C1 0.28304(4) 0.95743(5) 0.25349(4) 0.00955(10) Uani d 1 1
C C2 0.18775(5) 1.01423(5) 0.29565(4) 0.01021(10) Uani d 1 1
C C3 0.30791(5) 1.02291(6) 0.17184(4) 0.01333(11) Uani d 1 1
H H3A 0.3167(9) 1.1064(10) 0.1823(7) 0.024(3) Uiso d 1 1
H H3B 0.2509(10) 1.0133(10) 0.1323(7) 0.023(3) Uiso d 1 1
H H3C 0.3744(9) 0.9899(9) 0.1465(7) 0.020(2) Uiso d 1 1
C C4 0.26552(5) 0.82752(5) 0.23795(4) 0.01314(11) Uani d 1 1
H H4A 0.3291(9) 0.7933(10) 0.2120(7) 0.025(3) Uiso d 1 1
H H4B 0.2057(9) 0.8176(9) 0.1987(7) 0.020(2) Uiso d 1 1
H H4C 0.2505(8) 0.7861(9) 0.2889(7) 0.019(2) Uiso d 1 1
C C5 0.42313(5) 1.20239(5) 0.45830(4) 0.01192(11) Uani d 1 1
C C6 0.40175(5) 1.09179(5) 0.50964(4) 0.01110(11) Uani d 1 1
C C7 0.35561(7) 1.30226(7) 0.49223(5) 0.02424(16) Uani d 1 1
H H7A 0.3687(10) 1.3751(11) 0.4564(8) 0.033(3) Uiso d 1 1
H H7B 0.3770(11) 1.3184(12) 0.5514(9) 0.041(3) Uiso d 1 1
H H7C 0.2815(11) 1.2823(12) 0.4919(8) 0.036(3) Uiso d 1 1
C C8 0.53960(6) 1.23386(7) 0.45795(5) 0.01929(13) Uani d 1 1
H H8A 0.5830(10) 1.1701(11) 0.4330(8) 0.032(3) Uiso d 1 1
H H8B 0.5636(9) 1.2482(10) 0.5166(8) 0.030(3) Uiso d 1 1
H H8C 0.5506(9) 1.3071(10) 0.4247(7) 0.026(3) Uiso d 1 1
O O1W 0.51220(4) 0.74779(4) 0.26871(3) 0.01548(10) Uani d 1 1
H H1WA 0.5426(12) 0.7243(12) 0.2236(10) 0.046(4) Uiso d 1 1
H H1WB 0.4774(11) 0.6878(12) 0.2863(9) 0.041(3) Uiso d 1 1
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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O6 Li1 O1W 5_676 . 111.23(6)
O6 Li1 O1 5_676 . 107.84(6)
O1W Li1 O1 . . 113.25(6)
O6 Li1 O3 5_676 8_656 106.33(6)
O1W Li1 O3 . 8_656 108.83(6)
O1 Li1 O3 . 8_656 109.12(6)
C1 O1 B1 . . 110.28(5)
C1 O1 Li1 . . 125.99(5)
B1 O1 Li1 . . 123.51(5)
C2 O2 B1 . . 110.05(5)
C2 O3 Li1 . 8_556 138.72(6)
C5 O4 B1 . . 110.58(5)
C6 O5 B1 . . 109.87(5)
C6 O6 Li1 . 5_676 163.55(6)
O4 B1 O1 . . 114.25(5)
O4 B1 O5 . . 104.66(5)
O1 B1 O5 . . 112.74(5)
O4 B1 O2 . . 112.80(5)
O1 B1 O2 . . 104.22(5)
O5 B1 O2 . . 108.23(5)
O1 C1 C4 . . 111.01(5)
O1 C1 C3 . . 109.85(5)
C4 C1 C3 . . 111.74(5)
O1 C1 C2 . . 103.20(5)
C4 C1 C2 . . 111.60(5)
C3 C1 C2 . . 109.10(5)
O3 C2 O2 . . 123.33(6)
O3 C2 C1 . . 125.90(6)
O2 C2 C1 . . 110.74(5)
C1 C3 H3A . . 111.0(7)
C1 C3 H3B . . 109.8(7)
H3A C3 H3B . . 107.9(9)
C1 C3 H3C . . 109.2(6)
H3A C3 H3C . . 109.7(9)
H3B C3 H3C . . 109.3(10)
C1 C4 H4A . . 109.4(7)
C1 C4 H4B . . 109.1(6)
H4A C4 H4B . . 108.8(9)
C1 C4 H4C . . 112.0(6)
H4A C4 H4C . . 108.7(9)
H4B C4 H4C . . 108.7(9)
O4 C5 C8 . . 110.39(5)
O4 C5 C7 . . 110.42(6)
C8 C5 C7 . . 111.88(6)
O4 C5 C6 . . 102.84(5)
C8 C5 C6 . . 111.71(5)
C7 C5 C6 . . 109.24(6)
O6 C6 O5 . . 123.19(6)
O6 C6 C5 . . 125.87(6)
O5 C6 C5 . . 110.92(5)
C5 C7 H7A . . 108.7(7)
C5 C7 H7B . . 108.4(8)
H7A C7 H7B . . 109.3(11)
C5 C7 H7C . . 111.7(8)
H7A C7 H7C . . 110.3(11)
H7B C7 H7C . . 108.4(11)
C5 C8 H8A . . 111.6(7)
C5 C8 H8B . . 109.5(7)
H8A C8 H8B . . 108.8(10)
C5 C8 H8C . . 109.6(7)
H8A C8 H8C . . 109.0(10)
H8B C8 H8C . . 108.3(9)
Li1 O1W H1WA . . 124.8(9)
Li1 O1W H1WB . . 129.9(9)
H1WA O1W H1WB . . 104.7(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Li1 O1 . 1.9725(13) yes
Li1 O1W . 1.9487(13) yes
Li1 O3 8_656 2.0059(13) yes
Li1 O6 5_676 1.9155(13) yes
O1 C1 . 1.4366(7) ?
O1 B1 . 1.4498(8) ?
O2 C2 . 1.3086(7) ?
O2 B1 . 1.5094(8) ?
O3 C2 . 1.2268(7) ?
O3 Li1 8_556 2.0059(13) ?
O4 C5 . 1.4297(8) ?
O4 B1 . 1.4476(8) ?
O5 C6 . 1.3125(8) ?
O5 B1 . 1.4901(8) ?
O6 C6 . 1.2193(8) ?
O6 Li1 5_676 1.9155(13) ?
C1 C4 . 1.5169(8) ?
C1 C3 . 1.5251(9) ?
C1 C2 . 1.5263(8) ?
C3 H3A . 0.972(11) ?
C3 H3B . 0.963(12) ?
C3 H3C . 1.007(11) ?
C4 H4A . 0.987(12) ?
C4 H4B . 0.988(11) ?
C4 H4C . 0.953(11) ?
C5 C8 . 1.5223(9) ?
C5 C7 . 1.5228(10) ?
C5 C6 . 1.5238(9) ?
C7 H7A . 1.019(13) ?
C7 H7B . 0.993(14) ?
C7 H7C . 0.968(13) ?
C8 H8A . 0.994(13) ?
C8 H8B . 0.990(12) ?
C8 H8C . 0.997(12) ?
O1W H1WA . 0.854(16) ?
O1W H1WB . 0.861(14) ?
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_site_symmetry_1
_geom_torsion
O6 Li1 O1 C1 5_676 -163.76(5)
O1W Li1 O1 C1 . -40.24(9)
O3 Li1 O1 C1 8_656 81.15(8)
O6 Li1 O1 B1 5_676 22.04(9)
O1W Li1 O1 B1 . 145.56(6)
O3 Li1 O1 B1 8_656 -93.05(7)
C5 O4 B1 O1 . -132.62(5)
C5 O4 B1 O5 . -8.84(6)
C5 O4 B1 O2 . 108.60(6)
C1 O1 B1 O4 . -112.92(6)
Li1 O1 B1 O4 . 62.07(8)
C1 O1 B1 O5 . 127.75(5)
Li1 O1 B1 O5 . -57.25(8)
C1 O1 B1 O2 . 10.61(6)
Li1 O1 B1 O2 . -174.39(5)
C6 O5 B1 O4 . 2.75(6)
C6 O5 B1 O1 . 127.49(5)
C6 O5 B1 O2 . -117.77(5)
C2 O2 B1 O4 . 120.53(5)
C2 O2 B1 O1 . -3.95(6)
C2 O2 B1 O5 . -124.16(5)
B1 O1 C1 C4 . -132.19(5)
Li1 O1 C1 C4 . 52.96(8)
B1 O1 C1 C3 . 103.72(6)
Li1 O1 C1 C3 . -71.13(7)
B1 O1 C1 C2 . -12.51(6)
Li1 O1 C1 C2 . 172.64(6)
Li1 O3 C2 O2 8_556 -164.56(7)
Li1 O3 C2 C1 8_556 17.31(12)
B1 O2 C2 O3 . 177.79(6)
B1 O2 C2 C1 . -3.83(7)
O1 C1 C2 O3 . -171.56(6)
C4 C1 C2 O3 . -52.29(8)
C3 C1 C2 O3 . 71.68(8)
O1 C1 C2 O2 . 10.11(6)
C4 C1 C2 O2 . 129.38(5)
C3 C1 C2 O2 . -106.65(6)
B1 O4 C5 C8 . 130.06(6)
B1 O4 C5 C7 . -105.70(6)
B1 O4 C5 C6 . 10.76(6)
Li1 O6 C6 O5 5_676 172.88(18)
Li1 O6 C6 C5 5_676 -8.8(2)
B1 O5 C6 O6 . -177.52(6)
B1 O5 C6 C5 . 3.98(7)
O4 C5 C6 O6 . 172.41(6)
C8 C5 C6 O6 . 54.03(8)
C7 C5 C6 O6 . -70.29(8)
O4 C5 C6 O5 . -9.14(6)
C8 C5 C6 O5 . -127.51(6)
C7 C5 C6 O5 . 108.16(6)
