#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:25:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179663 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/16/4511666.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_4511666
loop_
_publ_author_name
'Downard, Andrew'
'Nieuwenhuyzen, Mark'
'Seddon, Kenneth R.'
'van den Berg, Jan-Albert'
'Schmidt, Michael A.'
'Vaughan, Julian F. S.'
'Welz-Biermann, Urs'
_publ_section_title
;
 Structural Features of Lithium Organoborates
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              111
_journal_paper_doi               10.1021/cg010035q
_journal_volume                  2
_journal_year                    2002
_chemical_formula_sum            'C14 H14 B Li N4 O6'
_chemical_formula_weight         352.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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-97
_cell_angle_alpha                105.778(3)
_cell_angle_beta                 92.193(4)
_cell_angle_gamma                112.421(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7941(17)
_cell_length_b                   9.9647(19)
_cell_length_c                   11.840(2)
_cell_measurement_temperature    153(2)
_cell_volume                     911.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.788
_diffrn_measured_fraction_theta_max 0.788
_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  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5203
_diffrn_reflns_theta_full        28.71
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.099
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.632
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.632
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.532
_refine_ls_shift/su_mean         0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2436
_refine_ls_wR_factor_ref         0.2517
_reflns_number_gt                2738
_reflns_number_total             3705
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg010035q.cif
_cod_data_source_block           libsbm
_cod_database_code               4511666
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
B1 B 0.6146(4) -0.0569(4) 0.2050(3) 0.0270(8) Uani 1 1 d
O1A O 0.6051(3) -0.0743(2) 0.07966(19) 0.0314(6) Uani 1 1 d
C2A C 0.6131(4) -0.2009(3) 0.0065(3) 0.0262(7) Uani 1 1 d
C3A C 0.5422(4) -0.2530(4) -0.1131(3) 0.0318(7) Uani 1 1 d
H3A H 0.492(5) -0.201(4) -0.139(3) 0.043(10) Uiso 1 1 d
C4A C 0.5506(5) -0.3815(4) -0.1879(3) 0.0355(8) Uani 1 1 d
H4A H 0.499(5) -0.420(4) -0.273(3) 0.035(9) Uiso 1 1 d
C5A C 0.6293(4) -0.4611(4) -0.1467(3) 0.0338(8) Uani 1 1 d
H5A H 0.639(5) -0.547(5) -0.202(4) 0.050(11) Uiso 1 1 d
C6A C 0.7001(4) -0.4091(4) -0.0291(3) 0.0305(7) Uani 1 1 d
H6A H 0.742(5) -0.472(4) -0.003(3) 0.033(9) Uiso 1 1 d
C7A C 0.6924(4) -0.2798(3) 0.0488(3) 0.0260(7) Uani 1 1 d
C8A C 0.7679(4) -0.2228(4) 0.1748(3) 0.0274(7) Uani 1 1 d
O81A O 0.7331(3) -0.1150(2) 0.24562(19) 0.0299(5) Uani 1 1 d
O82A O 0.8620(3) -0.2695(3) 0.2133(2) 0.0417(7) Uani 1 1 d
O1B O 0.6738(3) 0.1029(2) 0.2689(2) 0.0320(6) Uani 1 1 d
C2B C 0.5982(4) 0.1546(3) 0.3575(3) 0.0255(7) Uani 1 1 d
C3B C 0.6722(4) 0.3081(4) 0.4244(3) 0.0310(7) Uani 1 1 d
H3B H 0.778(5) 0.368(5) 0.405(3) 0.044(11) Uiso 1 1 d
C4B C 0.5966(5) 0.3635(4) 0.5153(3) 0.0349(8) Uani 1 1 d
H4B H 0.649(5) 0.465(4) 0.556(3) 0.035(10) Uiso 1 1 d
C5B C 0.4477(5) 0.2691(4) 0.5404(3) 0.0358(8) Uani 1 1 d
H5B H 0.396(5) 0.311(4) 0.607(3) 0.039(10) Uiso 1 1 d
C6B C 0.3738(4) 0.1178(4) 0.4729(3) 0.0307(7) Uani 1 1 d
H6B H 0.272(5) 0.053(4) 0.494(3) 0.044(11) Uiso 1 1 d
C7B C 0.4471(4) 0.0589(3) 0.3804(3) 0.0248(7) Uani 1 1 d
C8B C 0.3658(4) -0.1006(4) 0.3057(3) 0.0261(7) Uani 1 1 d
O81B O 0.4473(3) -0.1516(2) 0.2259(2) 0.0304(6) Uani 1 1 d
O82B O 0.2259(3) -0.1860(3) 0.3135(2) 0.0376(6) Uani 1 1 d
Li1 Li 0.0045(7) -0.3161(6) 0.3045(5) 0.0325(12) Uani 1 1 d
N1S N -0.0520(4) -0.5378(4) 0.2000(3) 0.0443(8) Uani 1 1 d
C2S C -0.0963(4) -0.6403(4) 0.1160(4) 0.0371(8) Uani 1 1 d
C3S C -0.1524(6) -0.7700(5) 0.0085(4) 0.0495(10) Uani 1 1 d
H31S H -0.072(9) -0.801(7) -0.015(6) 0.11(2) Uiso 1 1 d
H32S H -0.243(8) -0.860(7) 0.009(5) 0.086(17) Uiso 1 1 d
H33S H -0.222(9) -0.745(7) -0.050(6) 0.11(2) Uiso 1 1 d
N4S N -0.0428(4) -0.2857(4) 0.4762(3) 0.0467(8) Uani 1 1 d
C5S C -0.0603(4) -0.2396(5) 0.5719(4) 0.0413(9) Uani 1 1 d
C6S C -0.0842(6) -0.1823(6) 0.6931(4) 0.0544(12) Uani 1 1 d
H61S H -0.199(8) -0.215(6) 0.696(5) 0.082(16) Uiso 1 1 d
H62S H 0.009(10) -0.170(8) 0.735(6) 0.13(3) Uiso 1 1 d
H63S H -0.059(9) -0.061(9) 0.720(6) 0.12(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'
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'
O O 0.0106 0.0060 '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'
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
O1B B1 O1A 108.2(3) . .
O1B B1 O81B 114.2(2) . .
O1A B1 O81B 108.0(3) . .
O1B B1 O81A 108.0(3) . .
O1A B1 O81A 111.8(2) . .
O81B B1 O81A 106.7(2) . .
C2A O1A B1 118.0(2) . .
O1A C2A C7A 120.9(3) . .
O1A C2A C3A 119.5(3) . .
C7A C2A C3A 119.6(3) . .
C4A C3A C2A 119.6(3) . .
C3A C4A C5A 121.3(3) . .
C6A C5A C4A 119.1(3) . .
C5A C6A C7A 120.8(3) . .
C6A C7A C2A 119.6(3) . .
C6A C7A C8A 121.3(3) . .
C2A C7A C8A 119.1(3) . .
O82A C8A O81A 120.4(3) . .
O82A C8A C7A 122.4(3) . .
O81A C8A C7A 117.1(3) . .
C8A O81A B1 123.0(3) . .
C8A O82A Li1 167.8(3) . 1_655
C2B O1B B1 121.3(2) . .
O1B C2B C3B 118.4(3) . .
O1B C2B C7B 121.6(3) . .
C3B C2B C7B 120.0(3) . .
C2B C3B C4B 119.3(3) . .
C5B C4B C3B 121.4(3) . .
C6B C5B C4B 119.1(3) . .
C5B C6B C7B 120.8(3) . .
C2B C7B C6B 119.4(3) . .
C2B C7B C8B 119.7(3) . .
C6B C7B C8B 120.9(3) . .
O82B C8B O81B 119.6(3) . .
O82B C8B C7B 122.8(3) . .
O81B C8B C7B 117.7(3) . .
C8B O81B B1 124.4(2) . .
C8B O82B Li1 172.2(3) . .
O82B Li1 O82A 110.4(3) . 1_455
O82B Li1 N4S 106.7(3) . .
O82A Li1 N4S 111.2(3) 1_455 .
O82B Li1 N1S 112.6(3) . .
O82A Li1 N1S 98.9(3) 1_455 .
N4S Li1 N1S 116.9(3) . .
C2S N1S Li1 157.5(4) . .
N1S C2S C3S 179.5(4) . .
C5S N4S Li1 166.4(4) . .
N4S C5S C6S 179.4(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 O1B 1.435(4) .
B1 O1A 1.441(4) .
B1 O81B 1.487(4) .
B1 O81A 1.492(4) .
O1A C2A 1.350(3) .
C2A C7A 1.401(4) .
C2A C3A 1.396(5) .
C3A C4A 1.374(5) .
C4A C5A 1.396(5) .
C5A C6A 1.375(5) .
C6A C7A 1.393(4) .
C7A C8A 1.472(4) .
C8A O82A 1.219(4) .
C8A O81A 1.316(4) .
O82A Li1 1.889(6) 1_655
O1B C2B 1.353(3) .
C2B C3B 1.390(4) .
C2B C7B 1.397(4) .
C3B C4B 1.384(5) .
C4B C5B 1.389(5) .
C5B C6B 1.375(5) .
C6B C7B 1.398(4) .
C7B C8B 1.462(4) .
C8B O82B 1.224(4) .
C8B O81B 1.316(3) .
O82B Li1 1.862(6) .
Li1 O82A 1.889(6) 1_455
Li1 N4S 2.055(7) .
Li1 N1S 2.071(6) .
N1S C2S 1.139(5) .
C2S C3S 1.451(6) .
N4S C5S 1.141(5) .
C5S C6S 1.449(6) .
