#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/17/1511784.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1511784
loop_
_publ_author_name
'Han, Sang-Don'
'Allen, Joshua L.'
'Jónsson, Erlendur'
'Johansson, Patrik'
'McOwen, Dennis W.'
'Boyle, Paul D.'
'Henderson, Wesley A.'
_publ_section_title
;
 Solvate Structures and Computational/Spectroscopic Characterization of
 Lithium Difluoro(oxalato)borate (LiDFOB) Electrolytes
;
_journal_issue                   11
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              5521
_journal_paper_doi               10.1021/jp309102c
_journal_volume                  117
_journal_year                    2013
_chemical_formula_sum            'C8 H8 B F2 Li N2 O4'
_chemical_formula_weight         251.91
_chemical_name_systematic        ?
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_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                 113.8966(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.1948(2)
_cell_length_b                   15.6492(6)
_cell_length_c                   6.2164(2)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    110
_cell_measurement_theta_max      40.21
_cell_measurement_theta_min      3.58
_cell_volume                     550.98(3)
_computing_cell_refinement       SAINT
_computing_data_collection       Apex2
_computing_data_reduction        SAINT
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_computing_structure_refinement  XL
_computing_structure_solution    XS
_diffrn_ambient_temperature      110
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker-Nonius Kappa Axis X8 Apex2'
_diffrn_measurement_method       'omega and phi 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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            53001
_diffrn_reflns_theta_full        39.64
_diffrn_reflns_theta_max         43.52
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_correction_T_min  0.9420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0377
_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)+(0.0560P)²+0.0312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                3026
_reflns_number_total             3951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp309102c_si_002.cif
_cod_data_source_block           x11086
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               1511784
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
Li1 Li 0.6900(3) 0.2500 -0.0371(3) 0.0250(3) Uani 1 2 d S
O1 O 1.04315(7) 0.32580(2) 0.56710(7) 0.01605(7) Uani 1 1 d .
O2 O 0.83614(7) 0.34118(2) 0.79211(7) 0.01737(8) Uani 1 1 d .
C1 C 0.92838(7) 0.29889(3) 0.68990(8) 0.01308(8) Uani 1 1 d .
B1 B 1.13167(13) 0.2500 0.48009(14) 0.01598(12) Uani 1 2 d S
F1 F 1.03731(9) 0.2500 0.23696(8) 0.02257(10) Uani 1 2 d S
F2 F 1.37453(8) 0.2500 0.57217(10) 0.02300(10) Uani 1 2 d S
N1 N 0.53411(10) 0.15296(3) 0.08587(9) 0.02474(10) Uani 1 1 d .
C2 C 0.41945(9) 0.10860(3) 0.14283(9) 0.01947(9) Uani 1 1 d .
C3 C 0.27121(9) 0.05201(3) 0.21300(9) 0.01932(9) Uani 1 1 d .
H3A H 0.2342(17) 0.0004(6) 0.1092(17) 0.029(2) Uiso 1 1 d .
H3B H 0.1155(17) 0.0846(7) 0.1756(17) 0.031(2) Uiso 1 1 d .
C4 C 0.38806(8) 0.02591(3) 0.47245(9) 0.01589(8) Uani 1 1 d .
H4A H 0.4208(15) 0.0775(6) 0.5732(15) 0.0190(18) Uiso 1 1 d .
H4B H 0.2674(17) -0.0101(7) 0.5017(17) 0.027(2) Uiso 1 1 d .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1 Li1 N1 92.48(6) . 4_565
N1 Li1 F1 99.94(6) . .
N1 Li1 F1 99.94(6) 4_565 .
N1 Li1 O2 92.679(19) . 4_564
N1 Li1 O2 172.44(8) 4_565 4_564
F1 Li1 O2 84.59(5) . 4_564
N1 Li1 O2 172.44(8) . 1_554
N1 Li1 O2 92.679(19) 4_565 1_554
F1 Li1 O2 84.59(5) . 1_554
O2 Li1 O2 81.67(5) 4_564 1_554
N1 Li1 F2 93.54(6) . 1_454
N1 Li1 F2 93.54(6) 4_565 1_454
F1 Li1 F2 160.43(7) . 1_454
O2 Li1 F2 80.64(5) 4_564 1_454
O2 Li1 F2 80.64(5) 1_554 1_454
N1 Li1 C1 117.42(3) . 4_564
N1 Li1 C1 149.24(4) 4_565 4_564
F1 Li1 C1 82.76(5) . 4_564
O2 Li1 C1 24.81(2) 4_564 4_564
O2 Li1 C1 56.87(4) 1_554 4_564
F2 Li1 C1 78.44(5) 1_454 4_564
N1 Li1 C1 149.24(4) . 1_554
N1 Li1 C1 117.42(3) 4_565 1_554
F1 Li1 C1 82.76(5) . 1_554
O2 Li1 C1 56.87(4) 4_564 1_554
O2 Li1 C1 24.81(2) 1_554 1_554
F2 Li1 C1 78.44(5) 1_454 1_554
C1 Li1 C1 32.06(2) 4_564 1_554
C1 O1 B1 108.76(4) . .
C1 O2 Li1 105.97(4) . 1_556
O2 C1 O1 128.00(4) . .
O2 C1 C1 123.18(3) . 4_565
O1 C1 C1 108.81(2) . 4_565
O2 C1 Li1 49.22(3) . 1_556
O1 C1 Li1 176.97(4) . 1_556
C1 C1 Li1 73.971(12) 4_565 1_556
F2 B1 F1 111.21(6) . .
F2 B1 O1 110.40(4) . 4_565
F1 B1 O1 109.91(4) . 4_565
F2 B1 O1 110.40(4) . .
F1 B1 O1 109.91(4) . .
O1 B1 O1 104.83(5) 4_565 .
B1 F1 Li1 135.68(6) . .
B1 F2 Li1 135.96(6) . 1_656
C2 N1 Li1 169.24(6) . .
N1 C2 C3 179.40(6) . .
C2 C3 C4 112.91(4) . .
C2 C3 H3A 107.7(6) . .
C4 C3 H3A 110.5(6) . .
C2 C3 H3B 106.0(6) . .
C4 C3 H3B 111.7(5) . .
H3A C3 H3B 107.8(8) . .
C4 C4 C3 112.22(5) 3_656 .
C4 C4 H4A 110.9(5) 3_656 .
C3 C4 H4A 109.6(5) . .
C4 C4 H4B 109.6(6) 3_656 .
C3 C4 H4B 105.7(6) . .
H4A C4 H4B 108.6(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li1 N1 2.1027(11) .
Li1 N1 2.1027(11) 4_565
Li1 F1 2.1358(18) .
Li1 O2 2.1822(12) 4_564
Li1 O2 2.1822(12) 1_554
Li1 F2 2.4236(18) 1_454
Li1 C1 2.7707(15) 4_564
Li1 C1 2.7707(15) 1_554
O1 C1 1.3058(6) .
O1 B1 1.4969(6) .
O2 C1 1.2093(6) .
O2 Li1 2.1822(12) 1_556
C1 C1 1.5301(9) 4_565
C1 Li1 2.7707(15) 1_556
B1 F2 1.3760(9) .
B1 F1 1.3821(9) .
B1 O1 1.4969(6) 4_565
F2 Li1 2.4236(19) 1_656
N1 C2 1.1470(7) .
C2 C3 1.4637(7) .
C3 C4 1.5317(7) .
C3 H3A 1.000(10) .
C3 H3B 1.031(10) .
C4 C4 1.5210(9) 3_656
C4 H4A 0.992(9) .
C4 H4B 1.010(10) .
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_4
Li1 O2 C1 O1 -178.44(6) 1_556 .
Li1 O2 C1 C1 0.78(6) 1_556 4_565
B1 O1 C1 O2 178.29(5) . .
B1 O1 C1 C1 -1.02(4) . 4_565
B1 O1 C1 Li1 155.4(9) . 1_556
C1 O1 B1 F2 -117.31(5) . .
C1 O1 B1 F1 119.65(5) . .
C1 O1 B1 O1 1.58(7) . 4_565
F2 B1 F1 Li1 180.0 . .
O1 B1 F1 Li1 57.44(4) 4_565 .
O1 B1 F1 Li1 -57.44(4) . .
N1 Li1 F1 B1 -47.16(4) . .
N1 Li1 F1 B1 47.16(4) 4_565 .
O2 Li1 F1 B1 -138.94(2) 4_564 .
O2 Li1 F1 B1 138.94(2) 1_554 .
F2 Li1 F1 B1 180.0 1_454 .
C1 Li1 F1 B1 -163.839(12) 4_564 .
C1 Li1 F1 B1 163.839(12) 1_554 .
F1 B1 F2 Li1 180.0 . 1_656
O1 B1 F2 Li1 -57.72(4) 4_565 1_656
O1 B1 F2 Li1 57.72(4) . 1_656
N1 Li1 N1 C2 36.1(4) 4_565 .
F1 Li1 N1 C2 136.7(3) . .
O2 Li1 N1 C2 -138.3(3) 4_564 .
O2 Li1 N1 C2 -96.9(6) 1_554 .
F2 Li1 N1 C2 -57.6(4) 1_454 .
C1 Li1 N1 C2 -136.4(3) 4_564 .
C1 Li1 N1 C2 -130.8(3) 1_554 .
Li1 N1 C2 C3 58(6) . .
N1 C2 C3 C4 179(100) . .
C2 C3 C4 C4 -63.35(7) . 3_656
