#------------------------------------------------------------------------------
#$Date: 2017-03-05 07:21:17 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193849 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/19/7041995.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_7041995
loop_
_publ_author_name
'Finger, Lars H.'
'Venker, Alexander'
'Schröder, Fabian G'
'Sundermeyer, Jörg'
_publ_section_title
;
 New lithium borates with bistetrazolato(2-) and pyrazinediolato(2-)
 ligands - potentially interesting lithium electrolyte additives.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3014
_journal_page_last               3024
_journal_paper_doi               10.1039/c7dt00308k
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C10 H16 B F2 Li N8 O2'
_chemical_formula_sum            'C10 H16 B F2 Li N8 O2'
_chemical_formula_weight         336.06
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-06-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                107.287(13)
_cell_angle_beta                 101.500(13)
_cell_angle_gamma                97.456(13)
_cell_formula_units_Z            2
_cell_length_a                   8.1367(13)
_cell_length_b                   9.2057(16)
_cell_length_c                   11.0783(17)
_cell_measurement_reflns_used    4437
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      1.99
_cell_volume                     760.4(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. 
Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
Ortep-3 for Windows (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 
102, 53227 Bonn, Germany)
;
_computing_publication_material
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
ShelXle (C. B. Huebschle, G. M. Sheldrick, B. Dittrich, J. Appl. Cryst. 
2011, 44, 1281-1284)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R.
(2005). J. Appl. Cryst. 38, 381-388.)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6652
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.828
_diffrn_reflns_theta_min         1.989
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.762
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0361P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1528
_reflns_number_total             3209
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt00308k2.cif
_cod_data_source_block           lhf172
_cod_depositor_comments
'Adding full bibliography for 7041994--7042002.cif.'
_cod_database_code               7041995
_audit_contact_author            'Joerg Sundermeyer'
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.992
_solvent_exptl_crystal_recrystallization_method 'THF, diethyl ether'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.1251(3) 0.8729(3) 0.6291(2) 0.0478(5) Uani 1 1 d . .
C2 C 0.0325(3) 0.7573(2) 0.5027(2) 0.0479(5) Uani 1 1 d . .
C3 C 0.1037(3) 0.7214(3) 1.0853(2) 0.0620(7) Uani 1 1 d . .
H3A H 0.0019 0.6452 1.0791 0.074 Uiso 1 1 calc R U
H3B H 0.0768 0.8265 1.1103 0.074 Uiso 1 1 calc R U
C4 C 0.2575(3) 0.7140(3) 1.1861(2) 0.0615(6) Uani 1 1 d . .
H4A H 0.3257 0.8191 1.2385 0.074 Uiso 1 1 calc R U
H4B H 0.2208 0.6620 1.2456 0.074 Uiso 1 1 calc R U
C5 C 0.3586(3) 0.6189(3) 1.1026(2) 0.0593(6) Uani 1 1 d . .
H5A H 0.4819 0.6437 1.1476 0.071 Uiso 1 1 calc R U
H5B H 0.3143 0.5061 1.0786 0.071 Uiso 1 1 calc R U
C6 C 0.3280(3) 0.6707(3) 0.9856(2) 0.0662(7) Uani 1 1 d . .
H6A H 0.4044 0.7716 1.0034 0.079 Uiso 1 1 calc R U
H6B H 0.3481 0.5930 0.9093 0.079 Uiso 1 1 calc R U
C7 C -0.3499(3) 0.6029(3) 0.6565(2) 0.0566(6) Uani 1 1 d . .
H7A H -0.3927 0.4919 0.6421 0.068 Uiso 1 1 calc R U
H7B H -0.3138 0.6117 0.5783 0.068 Uiso 1 1 calc R U
C8 C -0.4877(3) 0.6956(3) 0.6823(2) 0.0660(7) Uani 1 1 d . .
H8A H -0.5502 0.7092 0.6013 0.079 Uiso 1 1 calc R U
H8B H -0.5705 0.6444 0.7188 0.079 Uiso 1 1 calc R U
C9 C -0.3886(3) 0.8487(3) 0.7799(2) 0.0677(7) Uani 1 1 d . .
H9A H -0.4610 0.9019 0.8334 0.081 Uiso 1 1 calc R U
H9B H -0.3414 0.9178 0.7362 0.081 Uiso 1 1 calc R U
C10 C -0.2470(3) 0.8011(3) 0.8622(2) 0.0642(7) Uani 1 1 d . .
H10A H -0.1450 0.8865 0.9019 0.077 Uiso 1 1 calc R U
H10B H -0.2862 0.7723 0.9326 0.077 Uiso 1 1 calc R U
Li1 Li 0.0292(5) 0.6601(4) 0.7886(4) 0.0535(9) Uani 1 1 d . .
B1 B 0.2333(4) 1.1110(3) 0.5556(3) 0.0527(7) Uani 1 1 d . .
N1 N 0.2072(2) 1.0177(2) 0.65079(17) 0.0481(5) Uani 1 1 d . .
N2 N 0.2714(2) 1.0827(2) 0.78204(19) 0.0547(5) Uani 1 1 d . .
N3 N 0.2286(2) 0.9793(2) 0.83501(18) 0.0546(5) Uani 1 1 d . .
N4 N 0.1367(2) 0.8452(2) 0.74103(18) 0.0511(5) Uani 1 1 d . .
N5 N 0.0815(2) 0.6270(2) 0.44871(18) 0.0504(5) Uani 1 1 d . .
N6 N -0.0416(2) 0.5522(2) 0.33684(18) 0.0521(5) Uani 1 1 d . .
N7 N -0.1612(2) 0.6322(2) 0.32231(18) 0.0523(5) Uani 1 1 d . .
N8 N -0.1175(2) 0.76274(19) 0.42704(17) 0.0476(5) Uani 1 1 d . .
F1 F 0.17387(15) 1.00946(13) 0.43071(12) 0.0530(3) Uani 1 1 d . .
F2 F 0.39973(16) 1.18490(14) 0.58701(12) 0.0585(4) Uani 1 1 d . .
O1 O 0.1497(2) 0.68553(19) 0.96215(15) 0.0603(4) Uani 1 1 d . .
O2 O -0.20837(19) 0.66835(17) 0.77134(15) 0.0582(4) Uani 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'
Li Li -0.0003 0.0001 '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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 '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'
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
N4 C1 N1 110.27(19) . .
N4 C1 C2 122.7(2) . .
N1 C1 C2 127.0(2) . .
N5 C2 N8 109.82(18) . .
N5 C2 C1 124.1(2) . .
N8 C2 C1 126.04(19) . .
O1 C3 C4 106.83(19) . .
O1 C3 H3A 110.4 . .
C4 C3 H3A 110.4 . .
O1 C3 H3B 110.4 . .
C4 C3 H3B 110.4 . .
H3A C3 H3B 108.6 . .
C5 C4 C3 103.07(19) . .
C5 C4 H4A 111.1 . .
C3 C4 H4A 111.1 . .
C5 C4 H4B 111.1 . .
C3 C4 H4B 111.1 . .
H4A C4 H4B 109.1 . .
C6 C5 C4 101.63(19) . .
C6 C5 H5A 111.4 . .
C4 C5 H5A 111.4 . .
C6 C5 H5B 111.4 . .
C4 C5 H5B 111.4 . .
H5A C5 H5B 109.3 . .
O1 C6 C5 104.9(2) . .
O1 C6 H6A 110.8 . .
C5 C6 H6A 110.8 . .
O1 C6 H6B 110.8 . .
C5 C6 H6B 110.8 . .
H6A C6 H6B 108.8 . .
O2 C7 C8 106.14(18) . .
O2 C7 H7A 110.5 . .
C8 C7 H7A 110.5 . .
O2 C7 H7B 110.5 . .
C8 C7 H7B 110.5 . .
H7A C7 H7B 108.7 . .
C9 C8 C7 103.3(2) . .
C9 C8 H8A 111.1 . .
C7 C8 H8A 111.1 . .
C9 C8 H8B 111.1 . .
C7 C8 H8B 111.1 . .
H8A C8 H8B 109.1 . .
C8 C9 C10 102.6(2) . .
C8 C9 H9A 111.2 . .
C10 C9 H9A 111.2 . .
C8 C9 H9B 111.2 . .
C10 C9 H9B 111.2 . .
H9A C9 H9B 109.2 . .
O2 C10 C9 104.60(19) . .
O2 C10 H10A 110.8 . .
C9 C10 H10A 110.8 . .
O2 C10 H10B 110.8 . .
C9 C10 H10B 110.8 . .
H10A C10 H10B 108.9 . .
O1 Li1 O2 113.3(2) . .
O1 Li1 N6 109.90(18) . 2_566
O2 Li1 N6 107.36(19) . 2_566
O1 Li1 N4 107.25(19) . .
O2 Li1 N4 106.15(18) . .
N6 Li1 N4 112.89(18) 2_566 .
F2 B1 F1 114.9(2) . .
F2 B1 N1 109.9(2) . .
F1 B1 N1 107.57(19) . .
F2 B1 N8 108.59(19) . 2_576
F1 B1 N8 107.5(2) . 2_576
N1 B1 N8 108.20(18) . 2_576
C1 N1 N2 106.46(17) . .
C1 N1 B1 131.95(19) . .
N2 N1 B1 121.59(18) . .
N3 N2 N1 107.80(17) . .
N2 N3 N4 110.17(18) . .
C1 N4 N3 105.31(18) . .
C1 N4 Li1 133.02(19) . .
N3 N4 Li1 121.38(18) . .
C2 N5 N6 105.02(17) . .
N7 N6 N5 111.23(17) . .
N7 N6 Li1 127.09(18) . 2_566
N5 N6 Li1 121.68(17) . 2_566
N6 N7 N8 106.87(18) . .
N7 N8 C2 107.06(16) . .
N7 N8 B1 121.55(19) . 2_576
C2 N8 B1 131.39(17) . 2_576
C3 O1 C6 108.00(17) . .
C3 O1 Li1 133.61(17) . .
C6 O1 Li1 118.38(17) . .
C7 O2 C10 109.64(16) . .
C7 O2 Li1 129.01(17) . .
C10 O2 Li1 116.49(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N4 1.326(3) .
C1 N1 1.340(3) .
C1 C2 1.465(3) .
C2 N5 1.322(2) .
C2 N8 1.352(3) .
C3 O1 1.442(3) .
C3 C4 1.526(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.520(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.496(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 O1 1.453(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 O2 1.445(3) .
C7 C8 1.516(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.502(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.517(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 O2 1.449(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
Li1 O1 1.906(4) .
Li1 O2 1.918(4) .
Li1 N6 2.063(4) 2_566
Li1 N4 2.068(4) .
B1 F2 1.360(3) .
B1 F1 1.367(3) .
B1 N1 1.574(3) .
B1 N8 1.581(3) 2_576
N1 N2 1.358(2) .
N2 N3 1.303(2) .
N3 N4 1.361(2) .
N5 N6 1.353(2) .
N6 N7 1.307(2) .
N6 Li1 2.063(4) 2_566
N7 N8 1.346(2) .
N8 B1 1.581(3) 2_576
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
N4 C1 C2 N5 -67.4(3) . .
N1 C1 C2 N5 113.1(3) . .
N4 C1 C2 N8 109.3(3) . .
N1 C1 C2 N8 -70.2(3) . .
O1 C3 C4 C5 -19.2(3) . .
C3 C4 C5 C6 35.1(2) . .
C4 C5 C6 O1 -39.1(2) . .
O2 C7 C8 C9 24.9(2) . .
C7 C8 C9 C10 -35.9(3) . .
C8 C9 C10 O2 34.3(2) . .
N4 C1 N1 N2 -0.4(2) . .
C2 C1 N1 N2 179.1(2) . .
N4 C1 N1 B1 -179.6(2) . .
C2 C1 N1 B1 -0.1(4) . .
F2 B1 N1 C1 -134.2(2) . .
F1 B1 N1 C1 -8.5(3) . .
N8 B1 N1 C1 107.3(2) 2_576 .
F2 B1 N1 N2 46.7(3) . .
F1 B1 N1 N2 172.50(17) . .
N8 B1 N1 N2 -71.7(2) 2_576 .
C1 N1 N2 N3 0.2(2) . .
B1 N1 N2 N3 179.43(18) . .
N1 N2 N3 N4 0.1(2) . .
N1 C1 N4 N3 0.5(2) . .
C2 C1 N4 N3 -179.02(19) . .
N1 C1 N4 Li1 174.11(19) . .
C2 C1 N4 Li1 -5.4(3) . .
N2 N3 N4 C1 -0.4(2) . .
N2 N3 N4 Li1 -174.91(17) . .
N8 C2 N5 N6 0.5(2) . .
C1 C2 N5 N6 177.7(2) . .
C2 N5 N6 N7 -0.1(2) . .
C2 N5 N6 Li1 179.62(19) . 2_566
N5 N6 N7 N8 -0.4(2) . .
Li1 N6 N7 N8 179.97(19) 2_566 .
N6 N7 N8 C2 0.6(2) . .
N6 N7 N8 B1 -179.60(18) . 2_576
N5 C2 N8 N7 -0.7(2) . .
C1 C2 N8 N7 -177.8(2) . .
N5 C2 N8 B1 179.6(2) . 2_576
C1 C2 N8 B1 2.4(4) . 2_576
C4 C3 O1 C6 -5.1(3) . .
C4 C3 O1 Li1 176.3(2) . .
C5 C6 O1 C3 28.0(3) . .
C5 C6 O1 Li1 -153.08(19) . .
C8 C7 O2 C10 -3.4(2) . .
C8 C7 O2 Li1 -157.4(2) . .
C9 C10 O2 C7 -19.4(2) . .
C9 C10 O2 Li1 138.2(2) . .
